Journal
CHEMICAL SCIENCE
Volume 13, Issue 12, Pages 3526-3532Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2sc00546h
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Funding
- Natural Science Foundation of Zhejiang Province [LY19B020016]
- K. C. Wong Education Foundation [GJTD-2020-08]
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A substrate-controlled regioselective functionalization of unactivated alkenes with trifluoroacetimidoyl chlorides has been developed to synthesize structurally diverse trifluoromethyl-containing indoles and indolines. The regioselectivity of the reaction is determined by the structure of the alkene substrates.
The synthesis of diverse products from the same starting materials is always attractive in organic chemistry. Here, a palladium-catalyzed substrate-controlled regioselective functionalization of unactivated alkenes with trifluoroacetimidoyl chlorides has been developed, which provides a direct but controllable access to a variety of structurally diverse trifluoromethyl-containing indoles and indolines. In more detail, with respect to gamma,delta-alkenes, 1,1-geminal difunctionalization of unactivated alkenes with trifluoroacetimidoyl chloride enables the [4 + 1] annulation to produce indoles; as for beta,gamma-alkenes, a [3 + 2] heteroannulation with the hydrolysis product of trifluoroacetimidoyl chloride through 1,2-vicinal difunctionalization of alkenes occurs to deliver indoline products. The structure of alkene substrates differentiates the regioselectivity of the reaction.
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