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Ni-Catalyzed Defluorination for the Synthesis of gem-Difluoro-1,3-dienes and Their [4 + 2] Cycloaddition Reaction

Author:
Zhou, Minqi, Zhang, Jian, Zhang, Xing-Guo, Zhang, Xingang
Source:
Organic letters 2019 v.21 no.3 pp. 671-674
ISSN:
1523-7052
Subject:
boron compounds, carbonates, chemical structure, cycloaddition reactions, organic compounds
Abstract:
A nickel-catalyzed defluorination of α-trifluoromethylated allyl/propargyl carbonates using bis(pinacolato)diboron (B₂pin₂) as a reactant is described. The reaction proceeds under relatively mild reaction conditions, providing conjugated gem-difluoroalkenes in moderate to good yields. Applications of the resulting 1,1-difluoro-1,3-dienes by [4 + 2] cycloaddition reactions with maleimide led to cyclic fluorinated products efficiently.
Agid:
6296635