Controllable access to trifluoromethyl-containing indoles and indolines: palladium-catalyzed regioselective functionalization of unactivated alkenes with trifluoroacetimidoyl chlorides |
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| Authors: | Hefei Yang Le-Cheng Wang Yu Zhang Dongling Zheng Zhengkai Chen Xiao-Feng Wu |
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| Institution: | Department of Chemistry, Key Laboratory of Surface & Interface Science of Polymer Materials of Zhejiang Province, Zhejiang Sci-Tech University, Hangzhou 310018 People''s Republic of China.; Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023 Liaoning China.; Leibniz-Institut für Katalyse e. V., Albert-Einstein-Straβe 29a, 18059 Rostock Germany, |
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| Abstract: | 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 γ,δ-alkenes, 1,1-geminal difunctionalization of unactivated alkenes with trifluoroacetimidoyl chloride enables the 4 + 1] annulation to produce indoles; as for β,γ-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.A palladium-catalyzed dual functionalization of unactivated alkenes with trifluoroacetimidoyl chlorides toward the synthesis of structurally diverse trifluoromethyl-containing indoles and indolines has been developed. |
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