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Palladium-Catalyzed Regioselective Difluoroalkylation and Carbonylation of Alkynes

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posted on 2016-05-18, 00:00 authored by Qiang Wang, Yu-Tao He, Jia-Hui Zhao, Yi-Feng Qiu, Lan Zheng, Jing-Yuan Hu, Yu-Chen Yang, Xue-Yuan Liu, Yong-Min Liang
A novel, four-component synthetic strategy to synthesize a series of β-difluoroalkyl unsaturated esters/amides with high regioslectivity is described. This Pd-catalyzed difluoroalkylation and carbonylation reaction can be carried out with simple starting materials. Through this protocol, two new C–C bonds (including one C–CF2 bond) and one C–O­(N) bond are constructed simultaneously in a single step. The synthetic utility of this reaction system has been certified by the applicability to a wide scope of alkynes and nucleophiles. Preliminary mechanistic studies suggest that the difluoroalkyl radical pathway is involved in this reaction.

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