Pd-Catalyzed α-Arylation of α,α-Difluoroketones with Aryl Bromides and Chlorides. A Route to Difluoromethylarenes

Journal of the American Chemical Society, Journal Year: 2014, Volume and Issue: 136(11), P. 4149 - 4152

Published: March 3, 2014

We report the Pd-catalyzed α-arylation of α,α-difluoroketones with aryl and heteroaryl bromides chlorides catalyzed by an air- moisture-stable palladacyclic complex containing P(t-Bu)Cy2 as ligand. The combination this arylation base-induced cleavage acyl–aryl C–C bond within α-aryl-α,α-difluoroketone constitutes a one-pot, two-step procedure to synthesize difluoromethylarenes from halides. A broad range electronically varied underwent these two transformations, providing α-aryl-α,α-difluoroketones, difluoromethylarenes, difluoromethylheteroarenes in high yields.

Language: Английский

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Suzuki-Miyaura Cross-Coupling of Unprotected, Nitrogen-Rich Heterocycles: Substrate Scope and Mechanistic Investigation

Journal of the American Chemical Society, Journal Year: 2013, Volume and Issue: 135(34), P. 12877 - 12885

Published: Aug. 2, 2013

The Suzuki-Miyaura cross-coupling of unprotected, nitrogen-rich heterocycles using precatalysts P1 or P2 is reported. procedure allows for the reaction variously substituted indazole, benzimidazole, pyrazole, indole, oxindole, and azaindole halides under mild conditions in good to excellent yields. Additionally, mechanism behind inhibitory effect unprotected azoles on Pd-catalyzed reactions described based evidence gained through experimental, crystallographic, theoretical investigations.

Language: Английский

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Biaryl monophosphine ligands in palladium-catalyzed C–N coupling: An updated User's guide

Tetrahedron, Journal Year: 2019, Volume and Issue: 75(32), P. 4199 - 4211

Published: May 11, 2019

Language: Английский

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N-Substituted 2-Aminobiphenylpalladium Methanesulfonate Precatalysts and Their Use in C–C and C–N Cross-Couplings

The Journal of Organic Chemistry, Journal Year: 2014, Volume and Issue: 79(9), P. 4161 - 4166

Published: April 11, 2014

A series of phosphine-ligated palladium precatalysts based on N-methyl- and N-phenyl-2-aminobiphenyl have been developed. Substitution at the nitrogen center prevents presence traces aminobiphenyls that contain a free -NH2 group from contaminating cross-coupling products. These produce N-substituted carbazoles upon activation, which cannot consume starting materials. were efficiently generated 2-aminobiphenyl with minimal purification found to be highly effective in Suzuki-Miyaura C-N reactions.

Language: Английский

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Catalytic Enantioselective Arylboration of Alkenylarenes

Angewandte Chemie International Edition, Journal Year: 2016, Volume and Issue: 56(3), P. 851 - 855

Published: Dec. 21, 2016

Abstract A method for the catalytic enantioselective arylboration of alkenylarenes is disclosed. The reaction leads to formation 1,1‐diarylalkanes that also incorporate an additional pinacol boronic ester which can be easily transformed a variety groups. products are formed with excellent diastereoselectivities and enantioselectivities.

Language: Английский

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