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Four‐Component Borocarbonylation of Vinylarenes Enabled by Cooperative Cu/Pd Catalysis: Access to β‐Boryl Ketones and β‐Boryl Vinyl Esters

Yang Yuan, Fu‐Peng Wu, Jian‐Xing Xu, Xiao‐Feng Wu

2020Angewandte Chemie International Edition66 citationsDOI

Abstract

Abstract We report here a general four‐component synthetic procedure for the preparation of β‐boryl ketones and β‐boryl vinyl esters. Joint catalyzed by palladium and copper catalysts, borocarbonylative reaction between vinylarenes, aryl halides/triflates, B 2 Pin 2 , and carbon monoxide proceed successfully. A variety of synthetically useful β‐boryl ketones were synthesized in good to high yields by using aryl iodides as the substrates. It is noteworthy that when aryl triflates were applied as the starting materials, β‐boryl vinyl esters were synthesized in a similar manner and with broad functional group tolerance. A rational mechanism for this reaction was also proposed.

Topics & Concepts

Component (thermodynamics)CatalysisChemistryOrganic chemistryPolymer chemistryPhysicsThermodynamicsOrganoboron and organosilicon chemistryCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization Methods
Four‐Component Borocarbonylation of Vinylarenes Enabled by Cooperative Cu/Pd Catalysis: Access to β‐Boryl Ketones and β‐Boryl Vinyl Esters | Litcius