0000000000907356
AUTHOR
Petra Vasko
Reactions of m-Terphenyl-Stabilized Germylene and Stannylene with Water and Methanol: Oxidative Addition versus Arene Elimination and Different Reaction Pathways for Alkyl- and Aryl-Substituted Species
Reactions of the divalent germylene Ge(ArMe6)2 (ArMe6 = C6H3-2,6-{C6H2-2,4,6-(CH3)3}2) with water or methanol gave the Ge(IV) insertion product (ArMe6)2Ge(H)OH (1) or (ArMe6)2Ge(H)OMe (2), respectively. In contrast, its stannylene congener Sn(ArMe6)2 reacted with water or methanol to produce the Sn(II) species {ArMe6Sn(μ-OH)}2 (3) or {ArMe6Sn(μ-OMe)}2 (4), respectively, with elimination of ArMe6H. Compounds 1–4 were characterized by IR and NMR spectroscopy as well as by X-ray crystallography. Density functional theory calculations yielded mechanistic insight into the formation of (ArMe6)2Ge(H)OH and {ArMe6Sn(μ-OH)}2. The insertion of an m-terphenyl-stabilized germylene into the O–H bond was…
Synthesis, characterization, and reactivity of heavier group 13 and 14 metallylenes and metalloid clusters : small molecule activation and more
Effects of Remote Ligand Substituents on the Structures, Spectroscopic, and Magnetic Properties of Two-Coordinate Transition-Metal Thiolate Complexes
The first-row transition-metal(II) dithiolates M(SAriPr4)2 [AriPr4 = C6H3-2,6-(C6H3-2,6-iPr2)2; M = Cr (1), Mn (3), Fe (4), Co (5), Ni (6), and Zn (7)] and Cr(SArMe6)2 [2; ArMe6 = C6H3-2,6-(C6H2-2,4,6-Me3)2] and the ligand-transfer reagent (NaSAriPr4)2 (8) are described. In contrast to their M(SAriPr6)2 (M = Cr, Mn, Fe, Co, Ni, and Zn; AriPr6 = C6H3-2,6-(C6H2-2,4,6-iPr3)2) congeners, which differ from 1 and 3-6 in having p-isopropyl groups on the flanking aryl rings of the terphenyl substituents, compounds 1 and 4-6 display highly bent coordination geometries with S-M-S angles of 109.802(2)° (1), 120.2828(3)° (4), 91.730(3)° (5), and 92.68(2)° (6) as well as relatively close metal-flanking …
Arene C−H Activation at Aluminium(I): meta Selectivity Driven by the Electronics of S N Ar Chemistry
The reactivity of the electron-rich anionic Al(I) ('aluminyl') compound K 2 [(NON)Al] 2 (NON = 4,5-bis(2,6-diisopropylanilido)-2,7-di- tert -butyl-9,9-dimethylxanthene) towards mono- and disubstituted arenes is reported. C-H activation chemistry with n -butylbenzene gives exclusively the product of activation at the arene meta position. Mechanistically, this transformation proceeds in a single step via a concerted Meisenheimer-type transition state. Selectivity is therefore based on similar electronic factors to classical S N Ar chemistry, which implies the destabilization of transition states featuring electron-donating groups in either the ortho or the para positions. In the cases of tolu…
The Aluminyl Anion : A New Generation of Aluminium Nucleophile
Trivalent aluminium compounds are well known for their reactivity as Lewis acids/electrophiles, a feature that is exploited in many pharmaceutical, industrial and laboratory-based reactions. Recently, a series of isolable aluminium(I) anions ('aluminyls') have been reported, which offer an alternative to this textbook description: these reagents behave as aluminium nucleophiles. This minireview covers the synthesis, structure and reactivity of aluminyl species reported to date, together with their associated metal complexes. The frontier orbitals of each of these species have been investigated using a common methodology to allow for a like-for-like comparison of their electronic structure a…
Cooperative N–H bond activation by amido-Ge(ii) cations
N-heterocyclic carbene (NHC) and tertiary phosphine-stabilized germylium-ylidene cations, [R(L)Ge:]+, featuring tethered amido substituents at R have been synthesized via halide abstraction. Characterization in the solid state by X-ray crystallography shows these systems to be monomeric, featuring a two-coordinate C,N- or P,N-ligated germanium atom. The presence of the strongly Lewis acidic cationic germanium centre and proximal amide function allows for facile cleavage of N-H bonds in 1,2-fashion: the products resulting from reactions with carbazole feature a tethered secondary amine donor bound to a three-coordinate carbazolyl-GeII centre. In each case, addition of the components of the N…
Carbon monoxide activation by a molecular aluminium imide: C-O bond cleavage and C-C bond formation
Anionic molecular imide complexes of aluminium are accessible via a rational synthetic approach involving the reactions of organo azides with a potassium aluminyl reagent. In the case of K2 [(NON)Al(NDipp)]2 (NON=4,5-bis(2,6-diisopropylanilido)-2,7-di-tert-butyl-9,9-dimethyl-xanthene; Dipp=2,6-diisopropylphenyl) structural characterization by X-ray crystallography reveals a short Al-N distance, which is thought primarily to be due to the low coordinate nature of the nitrogen centre. The Al-N unit is highly polar, and capable of the activation of relatively inert chemical bonds, such as those found in dihydrogen and carbon monoxide. In the case of CO, uptake of two molecules of the substrate…
Reversible O-H bond activation by an intramolecular frustrated Lewis pair
The interactions of the O–H bonds in alcohols, water and phenol with dimethylxanthene-derived frustrated Lewis pairs (FLPs) have been probed. Within the constraints of this backbone framework, the preference for adduct formation or O–H bond cleavage to give the corresponding zwitterion is largely determined by pKa considerations. In the case of the PPh2/B(C6F5)2 system and p-tBuC6H4OH, an equilibrium is established between the two isomeric forms which allows the thermodynamic parameters associated with zwitterion formation via O–H bond cleavage to be probed. peerReviewed
A nucleophilic gold complex.
Solid-state auride salts featuring the negatively charged Au– ion are known to be stable in the presence of alkali metal counterions. While such electron-rich species might be expected to be nucleophilic (in the same manner as I–, for example), their instability in solution means that this has not been verified experimentally. Here we report a two-coordinate gold complex (NON)AlAuPtBu3 (where NON is the chelating tridentate ligand 4,5-bis(2,6-diisopropylanilido)-2,7-di-tert-butyl-9,9-dimethylxanthene) that features a strongly polarized bond, Auδ––Alδ+. This is synthesized by reaction of the potassium aluminyl compound [K{Al(NON)}]2 with tBu3PAuI. Computational studies of the complex, includ…
Probing the Extremes of Covalency in M-Al bonds: Lithium and Zinc Aluminyl Compounds.
Synthetic routes to lithium, magnesium, and zinc aluminyl complexes are reported, allowing for the first structural characterization of an unsupported lithium-aluminium bond. Crystallographic and quantum-chemical studies are consistent with the presence of a highly polar Li-Al interaction, characterized by a low bond order and relatively little charge transfer from Al to Li. Comparison with magnesium and zinc aluminyl systems reveals changes to both the M-Al bond and the (NON)Al fragment (where NON=4,5-bis(2,6-diisopropylanilido)-2,7-di-tert-butyl-9,9-dimethylxanthene), consistent with a more covalent character, with the latter complex being shown to react with CO<sub>2</sub> vi…
Mechanistic Study of Stepwise Methylisocyanide Coupling and C-H Activation Mediated by a Low-Valent Main Group Molecule
An experimental and DFT investigation of the mechanism of the coupling of methylisocyanide and C-H activation mediated by the germylene (germanediyl) Ge(Ar(Me6))2 (Ar(Me6) = C6H3-2,6(C6H2-2,4,6-Me3)2) showed that it proceeded by initial MeNC adduct formation followed by an isomerization involving the migratory insertion of the MeNC carbon into the Ge-C ligand bond. Addition of excess MeNC led to sequential insertions of two further MeNC molecules into the Ge-C bond. The insertion of the third MeNC leads to methylisocyanide methyl group C-H activation to afford an azagermacyclopentadienyl species. The X-ray crystal structures of the 1:1 (Ar(Me6))2GeCNMe adduct, the first and final insertion …
Cleavage of Ge–Ge and Sn–Sn Triple Bonds in Heavy Group 14 Element Alkyne Analogues (EAriPr4)2 (E = Ge, Sn; AriPr4 = C6H3-2,6(C6H3-2,6-iPr2)2) by Reaction with Group 6 Carbonyls
The reactions of heavier group 14 element alkyne analogues (EAriPr4)2 (E = Ge, Sn; AriPr4 = C6H3-2,6-(C6H3-2,6-iPr2)2) with the group 6 transition-metal carbonyls M(CO)6 (M = Cr, Mo, W) under UV irradiation resulted in the cleavage of the E–E triple bond and the formation of the complexes {AriPr4EM(CO)4}2 (1–6), which were characterized by single crystal X-ray diffraction as well as by IR and multinuclear NMR spectroscopy. Single-crystal X-ray structural analyses of 1–6 showed that the complexes have a nearly planar rhomboid M2E2 core with three-coordinate group 14 atoms. The coordination geometry at the group 6 metals is distorted octahedral formed by four carbonyl groups as well as two br…
Trapping and Reactivity of a Molecular Aluminium Oxide Ion
Aluminium oxides constitute an important class of inorganic compound that are widely exploited in the chemical industry as catalysts and catalyst supports. Due to the tendency for such systems to aggregate via Al‐O‐Al bridges, the synthesis of well‐defined, soluble, molecular models for these materials is challenging. Here we show that reactions of the potassium aluminyl complex K 2 [( NON )Al] 2 ( NON = 4,5‐bis(2,6‐diiso‐propylanilido)‐2,7‐di‐tert‐butyl‐9,9‐dimethylxanthene) with CO 2 , PhNCO and N 2 O all proceed via a common aluminium oxide intermediate. This highly reactive species can be trapped by coordination of a THF molecule as the anionic oxide complex [( NON )AlO(THF)] ‐ , which …
A crystalline radical cation derived from Thiele’s hydrocarbon with redox range beyond 1 V
Thiele’s hydrocarbon occupies a central role as an open-shell platform for new organic materials, however little is known about its redox behaviour. While recent synthetic approaches involving symmetrical carbene substitution of the CPh2 termini yield isolable neutral/dicationic analogues, the intervening radical cations are much more difficult to isolate, due to narrow compatible redox ranges (typically 1 V), permitting its isolation in crystalline form. Further single-electron oxidation affords borenium dication 12+, thereby establishing an organoboron redox system fully characterized in all three redox states. We perceive that this strategy can be extended to other transient organic rad…
Addition of Ethylene or Hydrogen to a Main-Group Metal Cluster under Mild Conditions
Reaction of the tin cluster Sn8(Arinline image)4 (Arinline image=C6H2-2,6-(C6H3-2,4,6-Me3)2) with excess ethylene or dihydrogen at 25 °C/1 atmosphere yielded two new clusters that incorporated ethylene or hydrogen. The reaction with ethylene yielded Sn4(Arinline image)4(C2H2)5 that contained five ethylene moieties bridging four aryl substituted tin atoms and one tin–tin bond. Reaction with H2 produced a cyclic tin species of formula (Sn(H)Arinline image)4, which could also be synthesized by the reaction of {(Arinline image)Sn(μ-Cl)}2 with DIBAL-H. These reactions represent the first instances of direct reactions of isolable main-group clusters with ethylene or hydrogen under mild conditions…
Carbon Monoxide Activation by a Molecular Aluminium Imide: C−O Bond Cleavage and C−C Bond Formation
Anionic molecular imide complexes of aluminium are accessible via a rational synthetic approach involving the reactions of organo azides with a potassium aluminyl reagent. In the case of K 2 [( NON )Al(NDipp)] 2 ( NON = 4,5‐bis(2,6‐di iso propylanilido)‐2,7‐di‐tert‐butyl‐9,9‐dimethyl‐xanthene; Dipp = 2,6‐di iso propylphenyl) structural characterization by X‐ray crystallography reveals a short Al‐N distance, which is thought to be due primarily to the low coordinate nature of the nitrogen centre. The Al‐N unit is highly polar, and capable of the activation of relatively inert chemical bonds, such as those found in dihydrogen and carbon monoxide. In the case of CO, uptake of two molecules of …
Probing the non-innocent nature of an amino-functionalised β-diketiminate ligand in silylene/iminosilane systems
Electron-rich β-diketiminate ligands{,} featuring amino groups at the backbone β positions (“N-nacnac” ligands) have been employed in the synthesis of a range of silylene (SiII) complexes of the type (N-nacnac)SiX (where X = H{,} Cl{,} N(SiMe3)2{,} P(SiMe3)2 and Si(SiMe3)3). A combination of experimental and quantum chemical approaches reveals (i) that in all cases rearrangement to give an aza-butadienyl SiIV imide featuring a contracted five-membered heterocycle is thermodynamically favourable (and experimentally viable); (ii) that the kinetic lability of systems of the type (N-nacnac)SiX varies markedly as a function of X{,} such that compounds of this type can be isolated under ambient c…
Synthesis of new hybrid 1,4-thiazinyl-1,2,3-dithiazolyl radicals via Smiles rearrangement
The condensation reaction of 2-aminobenzenethiols and 3-aminopyrazinethiols with 2-amino-6-fluoro-N-methylpyridinium triflate afforded thioether derivatives that were found to undergo Smiles rearrangement and cyclocondensation with sulphur monochloride to yield new hybrid 1,4-thiazine-1,2,3-dithiazolylium cations. The synthesized cations were readily reduced to the corresponding stable neutral radicals with spin densities delocalized over both 1,4-thiazinyl and 1,2,3-dithiazolyl moieties. peerReviewed
The Instability of Ni{N(SiMe3 )2 }2 : A Fifty Year Old Transition Metal Silylamide Mystery.
The characterization of the unstable Ni(II) bis(silylamide) Ni{N(SiMe3 )2 }2 (1), its THF complex Ni{N(SiMe3 )2 }2 (THF) (2), and the stable bis(pyridine) derivative trans-Ni{N(SiMe3 )2 }2 (py)2 (3), is described. Both 1 and 2 decompose at ca. 25 °C to a tetrameric Ni(I) species, [Ni{N(SiMe3 )2 }]4 (4), also obtainable from LiN(SiMe3 )2 and NiCl2 (DME). Experimental and computational data indicate that the instability of 1 is likely due to ease of reduction of Ni(II) to Ni(I) and the stabilization of 4 through dispersion forces.
Controlling Oxidative Addition and Reductive Elimination at Tin(I) via Hemi-Lability.
We report on the synthesis of a distannyne supported by a pincer ligand bearing pendant amine donors that is capable of reversibly activating E–H bonds at one or both of the tin centres through dissociation of the hemi-labile N–Sn donor/acceptor interactions. This chemistry can be exploited to sequentially (and reversibly) assemble mixed-valence chains of tin atoms of the type ArSn{Sn(Ar)H} n SnAr ( n = 1, 2). The experimentally observed (decreasing) propensity towards chain growth with increasing chain length can be rationalized both thermodynamically and kinetically by the electron-withdrawing properties of the –Sn(Ar)H– backbone units generated via oxidative addition. peerReviewed
Reaction of LiArMe6 (ArMe6ArMe6 = C6H3-2,6-(C6H2-2,4,6-Me3)2) with indium(I)chloride yields three m-terphenyl stabilized mixed-valent organoindium subhalides
Indium(I)chloride reacts with LiArMe6 (ArMe6 = C6H3-2,6-(C6H2-2,4,6-Me3)2) in THF to give three new mixed-valent organoindium subhalides. While the 1:1 reaction of InCl with LiArMe6 yields the known metal-rich cluster In8(ArMe6)4 (1), the use of freshly prepared LiArMe6 led to incorporation of iodide, derived from the synthesis of LiArMe6, into the structures, to afford In4(ArMe6)4I2 (2) along with minor amounts of In3(ArMe6)3I2 (3). When the same reaction was performed in 4:3 stoichiometry, the mixed-halide compound In3(ArMe6)3ClI (4) was obtained. Further increasing the chloride:aryl ligand ratio resulted in the formation of the known mixed-halide species In4(ArMe6)4Cl2I2 that can also be…
A Germanium Isocyanide Complex Featuring (n → π*) Back-Bonding and Its Conversion to a Hydride/Cyanide Product via C-H Bond Activation under Mild Conditions
Reaction of the diarylgermylene Ge(ArMe6)2 [ArMe6 = C6H3-2,6-(C6H2-2,4,6-(CH3)3)2] with tert-butyl isocyanide gave the Lewis adduct species (ArMe6)2GeCNBut, in which the isocyanide ligand displays a decreased C–N stretching frequency consistent with an n → π* back-bonding interaction. Density functional theory confirmed that the HOMO is a Ge–C bonding combination between the lone pair of electrons on the germanium atom and the C–N π* orbital of the isocyanide ligand. The complex undergoes facile C–H bond activation to produce a new diarylgermanium hydride/cyanide species and isobutene via heterolytic cleavage of the N–But bond. peerReviewed
Probing the non-innocent nature of an amino-functionalised β-diketiminate ligand in silylene/iminosilane systems.
Electron-rich β-diketiminate ligands, featuring amino groups at the backbone β positions (“N-nacnac” ligands) have been employed in the synthesis of a range of silylene (SiII) complexes of the type (N-nacnac)SiX (where X = H, Cl, N(SiMe3)2, P(SiMe3)2 and Si(SiMe3)3). A combination of experimental and quantum chemical approaches reveals (i) that in all cases rearrangement to give an aza-butadienyl SiIV imide featuring a contracted five-membered heterocycle is thermodynamically favourable (and experimentally viable); (ii) that the kinetic lability of systems of the type (N-nacnac)SiX varies markedly as a function of X, such that compounds of this type can be isolated under ambient conditions …
Arene C‐H activation at aluminium(I) : meta selectivity driven by the electronics of SNAr chemistry
The reactivity of the electron-rich anionic Al(I) (‘aluminyl’) compound K 2 [(NON)Al] 2 (NON = 4,5-bis(2,6-diisopropylanilido)-2,7-di- tert -butyl-9,9-dimethylxanthene) towards mono- and disubstituted arenes is reported. C-H activation chemistry with n -butylbenzene gives exclusively the product of activation at the arene meta position. Mechanistically, this transformation proceeds in a single step via a concerted Meisenheimer-type transition state. Selectivity is therefore based on similar electronic factors to classical S N Ar chemistry, which implies the destabilization of transition states featuring electron-donating groups in either the ortho or the para positions. In the cases of tolu…
Reversible O–H bond activation by an intramolecular frustrated Lewis pair
The interactions of the O-H bonds in alcohols, water and phenol with dimethylxanthene-derived frustrated Lewis pairs (FLPs) have been probed. Within the constraints of this backbone framework, the preference for adduct formation or O-H bond cleavage to give the corresponding zwitterion is largely determined by pKa considerations. In the case of the PPh2/B(C6F5)2 system and p-tBuC6H4OH, an equilibrium is established between the two isomeric forms which allows the thermodynamic parameters associated with zwitterion formation via O-H bond cleavage to be probed.
Reversible, room-temperature C-C bond activation of benzene by an isolable metal complex
The activation of C-C bonds is of fundamental interest in the construction of complex molecules from petrochemical feedstocks. In the case of the archetypal aromatic hydrocarbon benzene, C-C cleavage is thermodynamically disfavoured, and is brought about only by transient highly reactive species generated in situ. Here we show that the oxidative addition of the C-C bond in benzene by an isolated metal complex is not only possible, but occurs at room temperature and reversibly at a single aluminium centre in [(NON)Al]- (where NON = 4,5-bis(2,6-diisopropylanilido)-2,7-di-tert-butyl-9,9-dimethylxanthene). Selectivity over C-H bond activation is achieved kinetically and allows for the generatio…
Cleavage of Ge–Ge and Sn–Sn Triple Bonds in Heavy Group 14 Element Alkyne Analogues (EAriPr4)2 (E = Ge, Sn; AriPr4 = C6H3-2,6(C6H3-2,6-iPr2)2) by Reaction with Group 6 Carbonyls
The reactions of heavier group 14 element alkyne analogues (EAriPr4)2 (E = Ge, Sn; AriPr4 = C6H3-2,6-(C6H3-2,6-iPr2)2) with the group 6 transition-metal carbonyls M(CO)6 (M = Cr, Mo, W) under UV irradiation resulted in the cleavage of the E–E triple bond and the formation of the complexes {AriPr4EM(CO)4}2 (1–6), which were characterized by single crystal X-ray diffraction as well as by IR and multinuclear NMR spectroscopy. Single-crystal X-ray structural analyses of 1–6 showed that the complexes have a nearly planar rhomboid M2E2 core with three-coordinate group 14 atoms. The coordination geometry at the group 6 metals is distorted octahedral formed by four carbonyl groups as well as two br…
Interactions of a Diplumbyne with Dinuclear Transition Metal Carbonyls to Afford Metalloplumbylenes
The metathesis reactions of the diplumbyne AriPr6PbPbAriPr6 (AriPr6 = −C6H3–2,6-(C6H2–2,4,6-iPr3)2) with the dinuclear metal carbonyls Mn2(CO)10, Fe2(CO)9, and Co2(CO)8 under mild conditions afforded the complexes Mn(CO)5(PbAriPr6) (1), Fe(CO)4(PbAriPr6)2 (2), and Co4(CO)9(PbAriPr6)2 (3), respectively. Complexes 1–3 were structurally characterized by single-crystal X-ray diffraction and spectroscopically characterized by 1H, 13C{1H}, 59Co{1H}, and 207Pb{1H} NMR; UV–vis; and IR methods. They are rare examples of species formed by the direct reaction of a group 14 dimetallyne with transition metal carbonyls. Complexes 1 and 2 feature Mn–Pb or Fe–Pb single bonds, whereas in 3 a Co–Pb cluster i…
Mechanistic Study of Stepwise Methylisocyanide Coupling and C-H Activation Mediated by a Low-Valent Main Group Molecule
An experimental and DFT investigation of the mechanism of the coupling of methylisocyanide and C–H activation mediated by the germylene (germanediyl) Ge(ArMe6)2 (ArMe6 = C6H3-2,6(C6H2-2,4,6-Me3)2) showed that it proceeded by initial MeNC adduct formation followed by an isomerization involving the migratory insertion of the MeNC carbon into the Ge–C ligand bond. Addition of excess MeNC led to sequential insertions of two further MeNC molecules into the Ge–C bond. The insertion of the third MeNC leads to methylisocyanide methyl group C–H activation to afford an azagermacyclopentadienyl species. The X-ray crystal structures of the 1:1 (ArMe6)2GeCNMe adduct, the first and final insertion produc…
Synthesis, structure and reaction chemistry of a nucleophilic aluminyl anion.
The reactivity of aluminium compounds is dominated by their electron deficiency and consequent electrophilicity; these compounds are archetypal Lewis acids (electron-pair acceptors). The main industrial roles of aluminium, and classical methods of synthesizing aluminium–element bonds (for example, hydroalumination and metathesis), draw on the electron deficiency of species of the type AlR3 and AlCl31,2. Whereas aluminates, [AlR4]−, are well known, the idea of reversing polarity and using an aluminium reagent as the nucleophilic partner in bond-forming substitution reactions is unprecedented, owing to the fact that low-valent aluminium anions analogous to nitrogen-, carbon- and boron-centred…
Reductions of M{N(SiMe3)2}3 (M = V, Cr, Fe): Terminal and Bridging Low-Valent First-Row Transition Metal Hydrido Complexes and “Metallo-Transamination”
The reaction of the vanadium(III) tris(silylamide) V{N(SiMe3)2}3 with LiAlH4 in diethyl ether gives the highly unstable mixed-metal polyhydride [V(μ2-H)6[Al{N(SiMe3)2}2]3][Li(OEt2)3] (1), which was structurally characterized. Alternatively, performing the same reaction in the presence of 12-crown-4 affords a rare example of a structurally verified vanadium terminal hydride complex, [VH{N(SiMe3)2}3][Li(12-crown-4)2] (2). The corresponding deuteride 2D was also prepared using LiAlD4. In contrast, no hydride complexes were isolated by reaction of M{N(SiMe3)2}3 (M = Cr, Fe) with LiAlH4 and 12-crown-4. Instead, these reactions afforded the anionic metal(II) complexes [M{N(SiMe3)2}3][Li(12-crown-…
Reactions of m-Terphenyl-Stabilized Germylene and Stannylene with Water and Methanol: Oxidative Addition versus Arene Elimination and Different Reaction Pathways for Alkyl- and Aryl-Substituted Species
Reactions of the divalent germylene Ge(ArMe6)2 (ArMe6 = C6H3-2,6-{C6H2-2,4,6-(CH3)3}2) with water or methanol gave the Ge(IV) insertion product (ArMe6)2Ge(H)OH (1) or (ArMe6)2Ge(H)OMe (2), respectively. In contrast, its stannylene congener Sn(ArMe6)2 reacted with water or methanol to produce the Sn(II) species {ArMe6Sn(μ-OH)}2 (3) or {ArMe6Sn(μ-OMe)}2 (4), respectively, with elimination of ArMe6H. Compounds 1–4 were characterized by IR and NMR spectroscopy as well as by X-ray crystallography. Density functional theory calculations yielded mechanistic insight into the formation of (ArMe6)2Ge(H)OH and {ArMe6Sn(μ-OH)}2. The insertion of an m-terphenyl-stabilized germylene into the O–H bond was…
Group 13 complexes of dipyridylmethane, a forgotten ligand in coordination chemistry.
The reactions of dipyridylmethane (dpma) with group 13 trichlorides were investigated in 1 : 1 and 1 : 2 molar ratios using NMR spectroscopy and X-ray crystallography. With 1 : 1 stoichiometry and Et2O as solvent, reactions employing AlCl3 or GaCl3 gave mixtures of products with the salt [(dpma)2MCl2](+)[MCl4](-) (M = Al, Ga) as the main species. The corresponding reactions in 1 : 2 molar ratio gave similar mixtures but with [(dpma)MCl2](+)[MCl4](-) as the primary product. Pure salts [(dpma)AlCl2](+)[Cl](-) and [(dpma)AlCl2](+)[AlCl4](-) could be obtained by performing the reactions in CH3CN. In the case of InCl3, a neutral monoadduct (dpma)InCl3 formed regardless of the stoichiometry emplo…
A Germanium Isocyanide Complex Featuring (n -> π*) Back-Bonding and Its Conversion to a Hydride/Cyanide Product via C–H Bond Activation under Mild Conditions
Reaction of the diarylgermylene Ge(Ar(Me(6)))(2) [Ar(Me(6)) = C(6)H(3)-2,6-(C(6)H(2)-2,4,6-(CH(3))(3))(2)] with tert-butyl isocyanide gave the Lewis adduct species (Ar(Me(6)))(2)GeCNBu(t), in which the isocyanide ligand displays a decreased C-N stretching frequency consistent with an n → π* back-bonding interaction. Density functional theory confirmed that the HOMO is a Ge-C bonding combination between the lone pair of electrons on the germanium atom and the C-N π* orbital of the isocyanide ligand. The complex undergoes facile C-H bond activation to produce a new diarylgermanium hydride/cyanide species and isobutene via heterolytic cleavage of the N-Bu(t) bond.
Cooperative N–H bond activation by amido-Ge(ii) cations
N-heterocyclic carbene (NHC) and tertiary phosphine-stabilized germylium-ylidene cations, [R(L)Ge:]+, featuring tethered amido substituents at R have been synthesized via halide abstraction. Characterization in the solid state by X-ray crystallography shows these systems to be monomeric, featuring a two-coordinate C,N- or P,N-ligated germanium atom. The presence of the strongly Lewis acidic cationic germanium centre and proximal amide function allows for facile cleavage of N–H bonds in 1,2-fashion: the products resulting from reactions with carbazole feature a tethered secondary amine donor bound to a three-coordinate carbazolyl-GeII centre. In each case, addition of the components of the N…
The Instability of Ni{N(SiMe3)2}2: A Fifty Year Old Transition Metal Silylamide Mystery
The characterization of the unstable NiII bis(silylamide) Ni{N(SiMe3)2}2 (1), its THF complex Ni{N(SiMe3)2}2(THF) (2), and the stable bis(pyridine) derivative trans-Ni{N(SiMe3)2}2(py)2 (3), is described. Both 1 and 2 decompose at ca. 25 °C to a tetrameric NiI species, [Ni{N(SiMe3)2}]4 (4), also obtainable from LiN(SiMe3)2 and NiCl2(DME). Experimental and computational data indicate that the instability of 1 is likely due to ease of reduction of NiII to NiI and the stabilization of 4 through dispersion forces. peerReviewed
Reversible, room-temperature C—C bond activation of benzene by an isolable metal complex
The activation of C-C bonds is of fundamental interest in the construction of complex molecules from petrochemical feedstocks. In the case of the archetypal aromatic hydrocarbon benzene, C-C cleavage is thermodynamically disfavored, and is brought about only by transient highly reactive species generated in situ. Here we show that the oxidative addition of the C-C bond in benzene by an isolated metal complex is not only possible, but occurs at room temperature and reversibly at a single aluminium center in [(NON)Al]- (where NON = 4,5-bis(2,6-diisopropylanilido)-2,7-di-tert-butyl-9,9-dimethylxanthene). Selectivity over C-H bond activation is achieved kinetically and allows for the generation…
Reaction of LiArMe6 (ArMe6= C6H3-2,6-(C6H2-2,4,6-Me3)2) with indium(I)chloride yields three m-terphenyl stabilized mixed-valent organoindium subhalides
Abstract Indium(I)chloride reacts with LiAr Me 6 ( Ar Me 6 = C6H3-2,6-(C6H2-2,4,6-Me3)2) in THF to give three new mixed-valent organoindium subhalides. While the 1:1 reaction of InCl with LiAr Me 6 yields the known metal-rich cluster In8( Ar Me 6 )4 (1), the use of freshly prepared LiAr Me 6 led to incorporation of iodide, derived from the synthesis of LiAr Me 6 , into the structures, to afford In4( Ar Me 6 )4I2 (2) along with minor amounts of In3( Ar Me 6 )3I2 (3). When the same reaction was performed in 4:3 stoichiometry, the mixed-halide compound In3( Ar Me 6 )3ClI (4) was obtained. Further increasing the chloride:aryl ligand ratio resulted in the formation of the known mixed-halide spe…
Approaching a “naked” boryl anion: amide metathesis as a route to calcium, strontium, and potassium boryl complexes
Abstract Amide metathesis has been used to generate the first structurally characterized boryl complexes of calcium and strontium, {(Me3Si)2N}M{B(NDippCH)2}(thf)n (M=Ca, n=2; M=Sr, n=3), through the reactions of the corresponding bis(amides), M{N(SiMe3)2}2(thf)2, with (thf)2Li‐ {B(NDippCH)2}. Most notably, this approach can also be applied to the analogous potassium amide K{N(SiMe3)2}, leading to the formation of the solvent‐free borylpotassium dimer [K{B(NDippCH)2}]2, which is stable in the solid state at room temperature for extended periods (48 h). A dimeric structure has been determined crystallographically in which the K+ cations interact weakly with both the ipso‐carbons of the flanki…
CCDC 1401116: Experimental Crystal Structure Determination
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CCDC 2094341: Experimental Crystal Structure Determination
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CCDC 1414953: Experimental Crystal Structure Determination
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CCDC 1401114: Experimental Crystal Structure Determination
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CCDC 1995924: Experimental Crystal Structure Determination
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CCDC 2058689: Experimental Crystal Structure Determination
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CCDC 1505083: Experimental Crystal Structure Determination
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CCDC 2095879: Experimental Crystal Structure Determination
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CCDC 1952095: Experimental Crystal Structure Determination
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CCDC 1414956: Experimental Crystal Structure Determination
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CCDC 2094344: Experimental Crystal Structure Determination
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CCDC 1899009: Experimental Crystal Structure Determination
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CCDC 1872784: Experimental Crystal Structure Determination
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CCDC 2008538: Experimental Crystal Structure Determination
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CCDC 1995922: Experimental Crystal Structure Determination
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CCDC 1854972: Experimental Crystal Structure Determination
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CCDC 1972056: Experimental Crystal Structure Determination
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CCDC 2070539: Experimental Crystal Structure Determination
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CCDC 1581596: Experimental Crystal Structure Determination
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CCDC 1995923: Experimental Crystal Structure Determination
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CCDC 1581598: Experimental Crystal Structure Determination
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CCDC 1036417: Experimental Crystal Structure Determination
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CCDC 1872783: Experimental Crystal Structure Determination
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CCDC 2005219: Experimental Crystal Structure Determination
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CCDC 1972053: Experimental Crystal Structure Determination
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CCDC 1970388: Experimental Crystal Structure Determination
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CCDC 1555899: Experimental Crystal Structure Determination
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CCDC 1505088: Experimental Crystal Structure Determination
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CCDC 2094340: Experimental Crystal Structure Determination
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CCDC 1828738: Experimental Crystal Structure Determination
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CCDC 2063254: Experimental Crystal Structure Determination
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CCDC 1899011: Experimental Crystal Structure Determination
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CCDC 1972057: Experimental Crystal Structure Determination
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CCDC 1899006: Experimental Crystal Structure Determination
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CCDC 1555900: Experimental Crystal Structure Determination
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CCDC 1943804: Experimental Crystal Structure Determination
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CCDC 1431125: Experimental Crystal Structure Determination
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CCDC 1519804: Experimental Crystal Structure Determination
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CCDC 1943806: Experimental Crystal Structure Determination
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CCDC 1505086: Experimental Crystal Structure Determination
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CCDC 2094342: Experimental Crystal Structure Determination
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CCDC 1972054: Experimental Crystal Structure Determination
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CCDC 2063252: Experimental Crystal Structure Determination
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CCDC 1972052: Experimental Crystal Structure Determination
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CCDC 1952092: Experimental Crystal Structure Determination
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CCDC 1401113: Experimental Crystal Structure Determination
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CCDC 1519805: Experimental Crystal Structure Determination
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CCDC 1505085: Experimental Crystal Structure Determination
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CCDC 954558: Experimental Crystal Structure Determination
Related Article: Zachary D. Brown , Petra Vasko , Jeremy D. Erickson , James C. Fettinger , Heikki M. Tuononen , and Philip P. Power|2013|J.Am.Chem.Soc.|135|6257|doi:10.1021/ja4003553
CCDC 1952094: Experimental Crystal Structure Determination
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CCDC 1943805: Experimental Crystal Structure Determination
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CCDC 1854971: Experimental Crystal Structure Determination
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CCDC 1536800: Experimental Crystal Structure Determination
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CCDC 2095878: Experimental Crystal Structure Determination
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CCDC 2095877: Experimental Crystal Structure Determination
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CCDC 1581594: Experimental Crystal Structure Determination
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CCDC 1854973: Experimental Crystal Structure Determination
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CCDC 1400650: Experimental Crystal Structure Determination
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CCDC 1899010: Experimental Crystal Structure Determination
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CCDC 1581591: Experimental Crystal Structure Determination
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CCDC 1414952: Experimental Crystal Structure Determination
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CCDC 2063253: Experimental Crystal Structure Determination
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CCDC 1431127: Experimental Crystal Structure Determination
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CCDC 1970386: Experimental Crystal Structure Determination
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CCDC 1872782: Experimental Crystal Structure Determination
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CCDC 1431126: Experimental Crystal Structure Determination
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CCDC 1943808: Experimental Crystal Structure Determination
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CCDC 1581600: Experimental Crystal Structure Determination
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CCDC 1505087: Experimental Crystal Structure Determination
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CCDC 954559: Experimental Crystal Structure Determination
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CCDC 2021078: Experimental Crystal Structure Determination
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CCDC 2074655: Experimental Crystal Structure Determination
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CCDC 2070550: Experimental Crystal Structure Determination
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CCDC 1581593: Experimental Crystal Structure Determination
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CCDC 1519808: Experimental Crystal Structure Determination
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CCDC 1414955: Experimental Crystal Structure Determination
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CCDC 2027035: Experimental Crystal Structure Determination
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CCDC 1581592: Experimental Crystal Structure Determination
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CCDC 1555898: Experimental Crystal Structure Determination
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CCDC 1872780: Experimental Crystal Structure Determination
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CCDC 1581599: Experimental Crystal Structure Determination
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CCDC 2005217: Experimental Crystal Structure Determination
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CCDC 2021077: Experimental Crystal Structure Determination
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CCDC 1952093: Experimental Crystal Structure Determination
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CCDC 2018925: Experimental Crystal Structure Determination
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CCDC 1555903: Experimental Crystal Structure Determination
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CCDC 1519806: Experimental Crystal Structure Determination
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CCDC 1952097: Experimental Crystal Structure Determination
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CCDC 2094346: Experimental Crystal Structure Determination
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CCDC 1943807: Experimental Crystal Structure Determination
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CCDC 2021075: Experimental Crystal Structure Determination
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CCDC 1899005: Experimental Crystal Structure Determination
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CCDC 1536801: Experimental Crystal Structure Determination
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CCDC 2094343: Experimental Crystal Structure Determination
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CCDC 1581595: Experimental Crystal Structure Determination
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CCDC 1420621: Experimental Crystal Structure Determination
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CCDC 2018923: Experimental Crystal Structure Determination
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