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Decarbonylative Suzuki–Miyaura Cross-Coupling of Aroyl Chlorides

Tongliang Zhou, Pei‐Pei Xie, Chong‐Lei Ji, Xin Hong, Michal Szostak

2020Organic Letters48 citationsDOIOpen Access PDF

Abstract

Herein, we report a catalyst system for Pd-catalyzed decarbonylative Suzuki-Miyaura cross-coupling of aroyl chlorides with boronic acids to furnish biaryls. This strategy is suitable for a broad range of common aroyl chlorides and boronic acids. The synthetic utility is highlighted in the direct late-stage functionalization of pharmaceuticals and natural products capitalizing on the presence of carboxylic acid moiety. Extensive mechanistic and DFT studies provide key insight into the reaction mechanism and high decarbonylative cross-coupling selectivity.

Topics & Concepts

ChemistryMoietyCombinatorial chemistryCatalysisBoronic acidOrganic chemistrySurface modificationPhysical chemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsChemical synthesis and alkaloids