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Rhodium-Catalyzed Carbonylative Coupling of Alkyl Halides with Phenols under Low CO Pressure

Han‐Jun Ai, Hai Wang, Chong‐Liang Li, Xiao‐Feng Wu

2020ACS Catalysis41 citationsDOI

Abstract

A rhodium-catalyzed carbonylative transformation of alkyl halides under low pressure of CO has been developed. This robust catalyst system allows using phenols as the carbonylative coupling partner and, meanwhile, exhibits high functional group tolerance and good chemoselectivity. Substrates even with a large steric hindrance group or multiple reaction sites can be selectively converted into the desired products in good to excellent yields. A gram-scale experiment was performed and delivered an almost quantitative amount of the product. Control experiments were performed as well, and a possible reaction mechanism is proposed.

Topics & Concepts

HalideAlkylCatalysisRhodiumCarbonylationChemistryChemoselectivitySteric effectsFunctional groupPhenolsCatalytic cycleOrganic chemistryCombinatorial chemistryCarbon monoxidePolymerCatalytic Cross-Coupling ReactionsCarbon dioxide utilization in catalysisCatalytic C–H Functionalization Methods
Rhodium-Catalyzed Carbonylative Coupling of Alkyl Halides with Phenols under Low CO Pressure | Litcius