0000000001307806
AUTHOR
Marine Labonde
Palladium-catalyzed heteroaryl thioethers synthesis overcoming palladium dithiolate resting states inertness: Practical road to sulfones and NH-sulfoximines
International audience; We provide efficient synthetic access to heteroaryl sulfones in two-steps using a simple palladium-1,1'-bis [(diphenyl)phosphanyl]ferrocene catalyst to form in high yields variously functionalized heteroaromatic thioethers. Pyridinyl-containing substrates can be subsequently selectively oxidized into sulfones and NH-sulfoximines by using very mild oxidation conditions with a high functional group tolerance. In the palladium catalyzed C-S coupling of heteroaromatic thiols, reactivity limitation is attached with electron-deficient thiols. We show that this limitation can be resolved by the successful use of 2-bromoheteroarenes in the C-S coupling. We established herein…
(2-Pyridyl)sulfonyl Groups for ortho -Directing Palladium- Catalyzed Carbon-Halogen Bond Formation at Functionalized Arenes
International audience; We describe an efficient palladium-catalyzed selective C-H ortho-monohalogenation (X=I, Br, Cl, F) of various functionalized (2-pyridyl) aryl-sulfones. ortho-, meta-and para-functionalization is tolerated at the arene group which undergoes C-H halogenation. Some modifications are also possible on the 2-(arylsulfonyl) heteroaryl directing groups. A comparison of the halogenation efficiency suggests that bromination is the practical method of choice, while chlorination and fluorination are possible but more challenging. Under forcing conditions ortho-dihalogenation can also be achieved.
Synthesis and Catalytic Use of Polar Phosphinoferrocene Amidosulfonates Bearing Bulky Substituents at the Ferrocene Backbone
International audience; Anionic phosphinoferrocene amidosulfonates bearing sterically demanding t-butyl substituents in positions 3 and 3' of the ferrocene scaffold, viz. rac-(Et3NH)[Fe(η5-tBuC5H3PR2)(η5-tBuC5H3C(O)NHCH2SO3)] (R = phenyl and cyclohexyl) were synthesized by amidation of the corresponding phosphinocarboxylic acids, [Fe(η5-tBuC5H3PR2)(η5-tBuC5H3CO2H)]. These ditopic polar phosphinoferrocenes and their non-t-butylated analogues have been used as lig-ands to prepare zwitterionic (η3-allyl)palladium(II) complexes [Pd(η3-C3H5){Fe(η5-R'C5H3PR2)(η5-R'C5H3C(O)NHCH2SO3)}] (R' = H, tBu, R = Ph, Cy). Depending on the isolation procedure and crystallization condi-tions, some complexes we…
CCDC 2077804: Experimental Crystal Structure Determination
Related Article: Petr Vosáhlo, Léa Radal, Marine Labonde, Ivana Císařová, Julien Roger, Nadine Pirio, Jean-Cyrille Hierso, Petr Štěpnička|2021|Organometallics|40|1934|doi:10.1021/acs.organomet.1c00244
CCDC 1558706: Experimental Crystal Structure Determination
Related Article: Johan Guilbaud, Marine Labonde, Hélène Cattey, Sylvie Contal, Christian Montalbetti, Nadine Pirio, Julien Roger, Jean-Cyrille Hierso|2017|Adv.Synth.Catal.|359|3792|doi:10.1002/adsc.201700858
CCDC 2077807: Experimental Crystal Structure Determination
Related Article: Petr Vosáhlo, Léa Radal, Marine Labonde, Ivana Císařová, Julien Roger, Nadine Pirio, Jean-Cyrille Hierso, Petr Štěpnička|2021|Organometallics|40|1934|doi:10.1021/acs.organomet.1c00244
CCDC 2077806: Experimental Crystal Structure Determination
Related Article: Petr Vosáhlo, Léa Radal, Marine Labonde, Ivana Císařová, Julien Roger, Nadine Pirio, Jean-Cyrille Hierso, Petr Štěpnička|2021|Organometallics|40|1934|doi:10.1021/acs.organomet.1c00244
CCDC 2077802: Experimental Crystal Structure Determination
Related Article: Petr Vosáhlo, Léa Radal, Marine Labonde, Ivana Císařová, Julien Roger, Nadine Pirio, Jean-Cyrille Hierso, Petr Štěpnička|2021|Organometallics|40|1934|doi:10.1021/acs.organomet.1c00244
CCDC 2077801: Experimental Crystal Structure Determination
Related Article: Petr Vosáhlo, Léa Radal, Marine Labonde, Ivana Císařová, Julien Roger, Nadine Pirio, Jean-Cyrille Hierso, Petr Štěpnička|2021|Organometallics|40|1934|doi:10.1021/acs.organomet.1c00244
CCDC 2077803: Experimental Crystal Structure Determination
Related Article: Petr Vosáhlo, Léa Radal, Marine Labonde, Ivana Císařová, Julien Roger, Nadine Pirio, Jean-Cyrille Hierso, Petr Štěpnička|2021|Organometallics|40|1934|doi:10.1021/acs.organomet.1c00244
CCDC 2077805: Experimental Crystal Structure Determination
Related Article: Petr Vosáhlo, Léa Radal, Marine Labonde, Ivana Císařová, Julien Roger, Nadine Pirio, Jean-Cyrille Hierso, Petr Štěpnička|2021|Organometallics|40|1934|doi:10.1021/acs.organomet.1c00244