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Pd/Cu‐Catalyzed Defluorinative Carbonylative Coupling of Aryl Iodides and <i>gem</i>‐Difluoroalkenes: Efficient Synthesis of α‐Fluorochalcones

Fu‐Peng Wu, Yang Yuan, Jiawang Liu, Xiao‐Feng Wu

2021Angewandte Chemie International Edition67 citationsDOI

Abstract

An unprecedented and challenging defluorinative carbonylation was achieved. Enabled by a Pd/Cu cooperative catalyst system, the first example of defluorinative carbonylative coupling has been established. With gem-difluoroalkenes and aryl iodides as the substrates, this methodology offers flexible and facile access to privileged α-fluorochalcones under mild reaction conditions in moderate-to-excellent yields. Mechanistic studies indicated transmetalation between palladium and copper intermediates as a crucial step of the catalytic cycle.

Topics & Concepts

TransmetalationArylCarbonylationCatalysisCombinatorial chemistryCatalytic cycleChemistryPalladiumCopperOrganic chemistryCarbon monoxideAlkylFluorine in Organic ChemistryInorganic Fluorides and Related CompoundsCarbon dioxide utilization in catalysis