4.8 Article

Palladium-Catalyzed Regioselective Difluoroalkylation and Carbonylation of Alkynes

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ORGANIC LETTERS
卷 18, 期 11, 页码 2664-2667

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b01038

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  1. National Science Foundation [NSF21272101, NSF21472073, NSF21472074, NSF21302076]
  2. Program for Changjiang Scholars and Innovative Research Team in University [IRT1138, IRT15R28]

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A novel, four-component synthetic strategy to synthesize a series of beta-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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