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Carbonylative Cross-Electrophile Coupling between Aryl Bromides and Aryl Triflates Enabled by Palladium and Rhodium Cooperative Catalysis and CO as Reductant

Gang Chen, Ruoxin Zhou, Xuemei Zhang, Xue Xiao, Søren Kramer, Gui‐Juan Cheng, Zhong Lian

2022ACS Catalysis24 citationsDOI

Abstract

Ketones are among the most useful functional groups in organic synthesis. Here, we report a carbonylative cross-electrophile coupling reaction that utilizes carbon monoxide gas as both carbonyl source and reductant. The use of Pd/Rh cooperative catalysis enables the carbonylative coupling of easily accessible aryl triflates and aryl bromides. Unlike previous carbonylative cross-electrophile coupling reactions, the method does not require addition of a stoichiometric metal reductant. Notably, density functional theory (DFT) calculations and isotope-labeling indicate that CO serves as the reductant.

Topics & Concepts

ElectrophileArylChemistryRhodiumCatalysisCarbon monoxideCarbonylationPalladiumCoupling reactionCombinatorial chemistryOrganic chemistryPhotochemistryAlkylCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsAsymmetric Hydrogenation and Catalysis