Copper-Catalyzed Regioselective Aminothiolation of Aromatic and Aliphatic Alkenes with N-Fluorobenzenesulfonimide and Thiols through Three-Component Radical Coupling

Masayuki Iwasaki, Kosei Nonaka, Song Zou, Yuta Sawanaka, Takaaki Shinozaki, Tomoya Fujii, Kiyohiko Nakajima, Yasushi Nishihara

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    6 Citations (Scopus)

    Abstract

    Copper-catalyzed regioselective aminothiolation of terminal and internal alkenes with N-fluorobenzenesulfonimide and thiols has been developed. The three-component reaction is promoted by the addition of dimethyl sulfide. In addition to aromatic alkenes, aliphatic alkenes are subjected to the reaction, affording various aminothiolation adducts as single regioisomers. The radical process is proposed by preliminary mechanistic studies, involving radical trap and radical clock experiments.

    Original languageEnglish
    Pages (from-to)15373-15379
    Number of pages7
    JournalJournal of Organic Chemistry
    Volume84
    Issue number23
    DOIs
    Publication statusPublished - Dec 6 2019

    ASJC Scopus subject areas

    • Organic Chemistry

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