Palladium-catalyzed peri -selective chalcogenation of naphthylamines with diaryl disulfides and diselenides via C-H bond cleavage

Masayuki Iwasaki, Wataru Kaneshika, Yuta Tsuchiya, Kiyohiko Nakajima, Yasushi Nishihara

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    127 Citations (Scopus)

    Abstract

    A palladium-catalyzed and picolinamide-directed C-H thiolation of naphthylamine derivatives with diaryl disulfides has been developed to provide a convenient route to 8-sulfenyl-1-naphthylamines. The reaction proceeds via a 5-membered palladacycle intermediates to afford the peri-thiolated products exclusively, in contrast to the conventional ortho-functionalization. Moreover, the related direct selenation was also achieved with diaryl diselenides, giving the corresponding selenated products with perfect site-selectivity.

    Original languageEnglish
    Pages (from-to)11330-11338
    Number of pages9
    JournalJournal of Organic Chemistry
    Volume79
    Issue number23
    DOIs
    Publication statusPublished - Dec 5 2014

    ASJC Scopus subject areas

    • Organic Chemistry

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