Zirconocene complexes bearing novel 3-dimethylamino-1,2-dihydropentalene derived ligand systems.

Coupling of the N,N-dimethylacrylamides 6a-c with cyclopentadienide resulted in the formation of the substituted 3-dimethylamino-1,2-dihydropentalnenes 2a-c. Deprotonation followed by metallation with CpZrCl(3)·DME gave the substituted zirconocenes 12a-c. The reaction of 3-dimethylamino-1-methyl-dihydropentalene 2a with ZrCl(2)(NMe(2))(2)·2THF resulted in a unique coupling between a pair of the aminodihydropentalene derivatives to yield an unsymmetrically bridged novel ansa-zirconocene framework (9a). Treatment of the 1,1-dimethyl-substituted substrate 2b with this Zr-amido reagent in contrast resulted in a clean deprotonation and formation of the unbridged bis(dimethylaminohydropentalenyl)…

Insertion Reactions of Neutral Phosphidozirconocene Complexes as a Convenient Entry into Frustrated Lewis Pair Territory

International audience; Neutral phosphidozirconocene complexes [Cp2Zr(PR2)Me] (Cp=cyclopentadienyl; 1a: R=cyclohexyl (Cy); 1b: R=mesityl (Mes); 1c: R=tBu) undergo insertion into the Zr-P bond by non-enolisable carbonyl building blocks (O=CRR), such as benzophenone, aldehydes, paraformaldehyde or CO2, to give [Cp2Zr(OCRRPR2)Me] (3-7). Depending on the steric bulk around P, complexes 3-7 react with B(C6F5)(3) to give O-bridged cationic zirconocene dimers that display typical frustrated Lewis pair (FLP)/ambiphilic ligand behaviour. Thus, the reaction of {[Cp2Zr(-OCHPhPCy2)][MeB(C6F5)(3)]}(2) (10a) with chalcone results in 1,4 addition of the Zr+/P FLP, whereas the reaction of {[Cp2Zr(-OCHFcPCy…

Versatile behavior of conjugated diynes with zirconocene reactive species

Thermal decomposition of Cp2ZrPh2 in the presence of the buta-1,3-diynes RC≡CC≡CR (R = Ph, SiMe3) can lead to seven- or five-membered metallacycles. In both cases a stable benzo-fused seven-membered zirconacyclocumulene arising from a 2-fold insertion of the triple bonds of the dialkyne in the in situ generated zirconocene benzyne is formed. In the case of Me3SiC≡CC≡CSiMe3 a second minor complex is isolated: a 3-alkynyl-substituted zirconaindene arising from a β monoinsertion of one acetylenic function of the conjugated diyne in the zirconocene benzyne. No stable 2-alkynyl-substituted zirconacycle was isolated. This α monoinsertion complex is an intermediate in the exchange of the metalated…

Phosphido- and Amidozirconocene Cation-Based Frustrated Lewis Pair Chemistry

Methyl abstraction from neutral [Cp2ZrMe(ERR')] complexes 1 (E = N, P; R, R' = alkyl, aryl) with either B(C6F5)3 or [Ph3C][B(C6F5)4] results in the formation of [Cp2Zr(ERR')][X] complexes 2 (X(-) = MeB(C6F5)3(-), B(C6F5)4(-)). The X-ray structure of amido complexes [Cp2Zr(NPh2)][MeB(C6F5)3] (2d) and [Cp2Zr(N(t)BuAr)][B(C6F5)4] (2e', Ar = 3,5-C6H3(CH3)2) is reported, showing a sterically dependent Zr/N-π interaction. Complexes 2 catalyze the hydrogenation of electron-rich olefins and alkynes under mild conditions (room temperature, 1.5 bar H2). Complex 2e binds CO2, giving [Cp2Zr(CO2)(N(t)BuAr)]2[MeB(C6F5)3]2 (3e). Amido complex 2d reacts with benzaldehyde yielding [Cp2Zr(OCH2Ph)((OC)PhNPh2)…

A Route toward (Aminomethyl)cyclopentadienide Ligands and Their Group 4 Metal Complexes

International audience

ChemInform Abstract: Phosphido- and Amidozirconocene Cation-Based Frustrated Lewis Pair Chemistry.

Methyl abstraction from neutral [Cp2ZrMe(ERR′)] complexes 1 (E = N, P; R, R′ = alkyl, aryl) with either B(C6F5)3 or [Ph3C][B(C6F5)4] results in the formation of [Cp2Zr(ERR′)][X] complexes 2 (X– = MeB(C6F5)3–, B(C6F5)4–). The X-ray structure of amido complexes [Cp2Zr(NPh2)][MeB(C6F5)3] (2d) and [Cp2Zr(NtBuAr)][B(C6F5)4] (2e′, Ar = 3,5-C6H3(CH3)2) is reported, showing a sterically dependent Zr/N−π interaction. Complexes 2 catalyze the hydrogenation of electron-rich olefins and alkynes under mild conditions (room temperature, 1.5 bar H2). Complex 2e binds CO2, giving [Cp2Zr(CO2)(NtBuAr)]2[MeB(C6F5)3]2 (3e). Amido complex 2d reacts with benzaldehyde yielding [Cp2Zr(OCH2Ph)((OC)PhNPh2)][MeB(C6F5…

Cyclizations via Frustrated Lewis Pairs: Lewis Acid Induced Intramolecular Additions of Amines to Olefins and Alkynes

Direct P-functionalization of azobenzene by a cationic phosphidozirconocene complex.

International audience; We report that the cationic phosphidozirconocene complex [(eta(5)-C5H5)(2)Zr(PCy2)][CH3B(C6F5)(3)] (II) reacts with azobenzene, resulting in the expedient formation of Zr complex (2) bound to a tridentate PNN ligand. This reaction proceeds by a mechanism of cooperative nucleophilic substitution of hydrogen. The intermediate sigma(H) adduct (1) has been characterized by NMR spectroscopy.

Synthetic Endeavors toward Titanium Based Frustrated Lewis Pairs with Controlled Electronic and Steric Properties

A new family of cationic Ti complexes 4′ with a pendant phosphine of general formula [CpCpPTiOAr][BPh4] (Cp = η5-C5H5; CpP = η5-C5H4(CMe2)PR2) has been prepared in four steps from 6,6-dimethylfulvene. These complexes were designed to behave as Ti based frustrated Lewis pairs (FLPs). The key synthetic step is a reduction–oxidation sequence from [CpCpPTiClOAr] complexes 3 using lithium phosphide salts as the reductants and ferricinium tetraphenylborate as the oxidant. Four complexes have been structurally characterized by X-ray diffraction and show elongated Ti–P bonds, above 2.60 A. One complex (4b′: OAr = 2,6-Me2C6H3; PR2 = PCy2) reacted with benzaldehyde to form a typical FLP activation pr…

The Taming of Redox‐Labile Phosphidotitanocene Cations

International audience; Tame d0 phosphidotitanocene cations stabilized with a pendant tertiary phosphane arm are reported. These compounds were obtained by one-electron oxidation of d1 precursors with [Cp2Fe][BPh4]. The electronic structure of these compounds was studied experimentally (EPR, UV/Vis, and NMR spectroscopy, X-ray diffraction analysis) and through DFT calculations. The theoretical analysis of the bonding situation by using the electron localization function (ELF) shows the presence of π-interactions between the phosphido ligand and Ti in the d0 complexes, whereas dπ–pπ repulsion prevents such interactions in the d1 complexes. In addition, CH–π interactions were observed in seve…

Cover Feature: A Route toward (Aminomethyl)cyclopentadienide Ligands and Their Group 4 Metal Complexes (Eur. J. Inorg. Chem. 34/2018)

CCDC 1421130: Experimental Crystal Structure Determination

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CCDC 1424182: Experimental Crystal Structure Determination

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CCDC 1871410: Experimental Crystal Structure Determination

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CCDC 1871415: Experimental Crystal Structure Determination

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CCDC 1871416: Experimental Crystal Structure Determination

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CCDC 1871408: Experimental Crystal Structure Determination

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CCDC 1825467: Experimental Crystal Structure Determination

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CCDC 1053357: Experimental Crystal Structure Determination

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CCDC 1825466: Experimental Crystal Structure Determination

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CCDC 1424183: Experimental Crystal Structure Determination

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CCDC 1424177: Experimental Crystal Structure Determination

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CCDC 1825460: Experimental Crystal Structure Determination

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CCDC 1052598: Experimental Crystal Structure Determination

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CCDC 1421134: Experimental Crystal Structure Determination

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CCDC 1825463: Experimental Crystal Structure Determination

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CCDC 1052596: Experimental Crystal Structure Determination

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CCDC 1871418: Experimental Crystal Structure Determination

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CCDC 1871412: Experimental Crystal Structure Determination

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CCDC 1421135: Experimental Crystal Structure Determination

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CCDC 1825459: Experimental Crystal Structure Determination

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CCDC 1052597: Experimental Crystal Structure Determination

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CCDC 1871414: Experimental Crystal Structure Determination

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CCDC 1052593: Experimental Crystal Structure Determination

Related Article: Adrien T. Normand, Philippe Richard, Cédric Balan, Constantin G. Daniliuc, Gerald Kehr, Gerhard Erker, Pierre Le Gendre|2015|Organometallics|34|2000|doi:10.1021/acs.organomet.5b00250

CCDC 1421138: Experimental Crystal Structure Determination

Related Article: Adrien T. Normand, Constantin G. Daniliuc, Birgit Wibbeling, Gerald Kehr, Pierre Le Gendre, and Gerhard Erker|2015|J.Am.Chem.Soc.|137|10796|doi:10.1021/jacs.5b06551

CCDC 1053358: Experimental Crystal Structure Determination

Related Article: Adrien T. Normand, Philippe Richard, Cédric Balan, Constantin G. Daniliuc, Gerald Kehr, Gerhard Erker, Pierre Le Gendre|2015|Organometallics|34|2000|doi:10.1021/acs.organomet.5b00250

CCDC 1825465: Experimental Crystal Structure Determination

Related Article: Quentin Bonnin, Sook-Yen Wong, Cedric Balan, Virginie Comte, Raluca Malacea, Marie-Jose Penouilh, Philippe Richard, Gerald Kehr, Adrien T. Normand, Gerhard Erker, Pierre Le Gendre|2018|Eur.J.Inorg.Chem.|2018|3813|doi:10.1002/ejic.201800636

CCDC 1871411: Experimental Crystal Structure Determination

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CCDC 1421133: Experimental Crystal Structure Determination

Related Article: Adrien T. Normand, Constantin G. Daniliuc, Birgit Wibbeling, Gerald Kehr, Pierre Le Gendre, and Gerhard Erker|2015|J.Am.Chem.Soc.|137|10796|doi:10.1021/jacs.5b06551

CCDC 1424181: Experimental Crystal Structure Determination

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CCDC 1052592: Experimental Crystal Structure Determination

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CCDC 1871409: Experimental Crystal Structure Determination

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CCDC 1421131: Experimental Crystal Structure Determination

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CCDC 1052595: Experimental Crystal Structure Determination

Related Article: Adrien T. Normand, Philippe Richard, Cédric Balan, Constantin G. Daniliuc, Gerald Kehr, Gerhard Erker, Pierre Le Gendre|2015|Organometallics|34|2000|doi:10.1021/acs.organomet.5b00250

CCDC 1052594: Experimental Crystal Structure Determination

Related Article: Adrien T. Normand, Philippe Richard, Cédric Balan, Constantin G. Daniliuc, Gerald Kehr, Gerhard Erker, Pierre Le Gendre|2015|Organometallics|34|2000|doi:10.1021/acs.organomet.5b00250

CCDC 1825462: Experimental Crystal Structure Determination

Related Article: Quentin Bonnin, Sook-Yen Wong, Cedric Balan, Virginie Comte, Raluca Malacea, Marie-Jose Penouilh, Philippe Richard, Gerald Kehr, Adrien T. Normand, Gerhard Erker, Pierre Le Gendre|2018|Eur.J.Inorg.Chem.|2018|3813|doi:10.1002/ejic.201800636

CCDC 1421128: Experimental Crystal Structure Determination

Related Article: Adrien T. Normand, Constantin G. Daniliuc, Birgit Wibbeling, Gerald Kehr, Pierre Le Gendre, and Gerhard Erker|2015|J.Am.Chem.Soc.|137|10796|doi:10.1021/jacs.5b06551

CCDC 1421129: Experimental Crystal Structure Determination

Related Article: Adrien T. Normand, Constantin G. Daniliuc, Birgit Wibbeling, Gerald Kehr, Pierre Le Gendre, and Gerhard Erker|2015|J.Am.Chem.Soc.|137|10796|doi:10.1021/jacs.5b06551

CCDC 1871417: Experimental Crystal Structure Determination

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CCDC 1825461: Experimental Crystal Structure Determination

Related Article: Quentin Bonnin, Sook-Yen Wong, Cedric Balan, Virginie Comte, Raluca Malacea, Marie-Jose Penouilh, Philippe Richard, Gerald Kehr, Adrien T. Normand, Gerhard Erker, Pierre Le Gendre|2018|Eur.J.Inorg.Chem.|2018|3813|doi:10.1002/ejic.201800636

CCDC 1421132: Experimental Crystal Structure Determination

Related Article: Adrien T. Normand, Constantin G. Daniliuc, Birgit Wibbeling, Gerald Kehr, Pierre Le Gendre, and Gerhard Erker|2015|J.Am.Chem.Soc.|137|10796|doi:10.1021/jacs.5b06551

CCDC 1825458: Experimental Crystal Structure Determination

Related Article: Quentin Bonnin, Sook-Yen Wong, Cedric Balan, Virginie Comte, Raluca Malacea, Marie-Jose Penouilh, Philippe Richard, Gerald Kehr, Adrien T. Normand, Gerhard Erker, Pierre Le Gendre|2018|Eur.J.Inorg.Chem.|2018|3813|doi:10.1002/ejic.201800636

CCDC 1424178: Experimental Crystal Structure Determination

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CCDC 1440373: Experimental Crystal Structure Determination

Related Article: Adrien T. Normand, Constantin G. Daniliuc, Gerald Kehr, Pierre Le Gendre, Gerhard Erker|2016|Dalton Trans.|45|3711|doi:10.1039/C6DT00416D

CCDC 1825464: Experimental Crystal Structure Determination

Related Article: Quentin Bonnin, Sook-Yen Wong, Cedric Balan, Virginie Comte, Raluca Malacea, Marie-Jose Penouilh, Philippe Richard, Gerald Kehr, Adrien T. Normand, Gerhard Erker, Pierre Le Gendre|2018|Eur.J.Inorg.Chem.|2018|3813|doi:10.1002/ejic.201800636

CCDC 1424179: Experimental Crystal Structure Determination

Related Article: Adrien T. Normand, Constantin G. Daniliuc, Birgit Wibbeling, Gerald Kehr, Pierre Le Gendre, Gerhard Erker|2016|Chem.-Eur.J.|22|4285|doi:10.1002/chem.201504792

CCDC 1440372: Experimental Crystal Structure Determination

Related Article: Adrien T. Normand, Constantin G. Daniliuc, Gerald Kehr, Pierre Le Gendre, Gerhard Erker|2016|Dalton Trans.|45|3711|doi:10.1039/C6DT00416D

CCDC 1421136: Experimental Crystal Structure Determination

Related Article: Adrien T. Normand, Constantin G. Daniliuc, Birgit Wibbeling, Gerald Kehr, Pierre Le Gendre, and Gerhard Erker|2015|J.Am.Chem.Soc.|137|10796|doi:10.1021/jacs.5b06551

CCDC 1871413: Experimental Crystal Structure Determination

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CCDC 1424180: Experimental Crystal Structure Determination

Related Article: Adrien T. Normand, Constantin G. Daniliuc, Birgit Wibbeling, Gerald Kehr, Pierre Le Gendre, Gerhard Erker|2016|Chem.-Eur.J.|22|4285|doi:10.1002/chem.201504792

CCDC 1424184: Experimental Crystal Structure Determination

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CCDC 1421137: Experimental Crystal Structure Determination

Related Article: Adrien T. Normand, Constantin G. Daniliuc, Birgit Wibbeling, Gerald Kehr, Pierre Le Gendre, and Gerhard Erker|2015|J.Am.Chem.Soc.|137|10796|doi:10.1021/jacs.5b06551