Copper/Photoredox-Catalyzed Regioselective 1, 4-Addition to 1, 3-Enynes: A Convenient Access to Perfluoroalkylated Allenes

Ya Chen; Quanyuan Wanga; Keyi Penga; Lilei Chenga; Ziyi Shea; Guo-Jun Deng

doi:10.1002/cjoc.202400207

Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (17) : 2023 -2028. DOI: 10.1002/cjoc.202400207

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Copper/Photoredox-Catalyzed Regioselective 1, 4-Addition to 1, 3-Enynes: A Convenient Access to Perfluoroalkylated Allenes

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Abstract

A general and broadly applicable copper and photoredox dual-catalyzed multicomponent 1, 4-perfluoroalkylcyanation of 1, 3-enynes has been developed. This protocol enjoys success with high regioselectivity, mild reaction conditions, and excellent functional-group tolerance, allowing the facile synthesis of structurally diverse perfluoroalkylated allenes from readily available fluoroalkyl halides, 1, 3-enynes and TMSCN in a one-pot manner. A reasonable mechanism has been proposed according to a series of control experiments.

Keywords

Fluorinated allenes / 1, 3-Enynes / Photoredox / Fluoroalkylation / Multicomponent reactions / Difunctionalization / Radicals / Regioselectivity

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Ya Chen, Quanyuan Wanga, Keyi Penga, Lilei Chenga, Ziyi Shea, Guo-Jun Deng. Copper/Photoredox-Catalyzed Regioselective 1, 4-Addition to 1, 3-Enynes: A Convenient Access to Perfluoroalkylated Allenes. Chinese Journal of Chemistry, 2024, 42(17): 2023-2028 DOI:10.1002/cjoc.202400207