New entry to the synthesis of α-iminonitriles by Lewis acid mediated isomerization of cyano-substituted iminoisobenzofurans prepared by palladium-catalyzed three-component coupling of arynes, isocyanides, and cyanoformates

Jing Li, Shintaro Noyori, Kiyohiko Nakajima, Yasushi Nishihara

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    17 Citations (Scopus)

    Abstract

    A variety of α-iminonitriles were formed as the minor products of three-component coupling reactions of arynes, isocyanides, and cyanoformates in the presence of the cationic palladium complex [Pd(NCPh)2(dppf)] (BF4)2 as the catalyst, along with cyano-substituted iminoisobenzofurans as the major products. α-Iminonitriles obtained from this process are hardly accessible by conventional methods. In addition, when the isolated iminoisobenzofurans were treated with diisobutylaluminum hydride (DIBAL-H) or AlMe3, the transformation of cyano-substituted iminoisobenzofurans into α-iminonitriles was observed.

    Original languageEnglish
    Pages (from-to)3500-3507
    Number of pages8
    JournalOrganometallics
    Volume33
    Issue number13
    DOIs
    Publication statusPublished - Jul 14 2014

    ASJC Scopus subject areas

    • Physical and Theoretical Chemistry
    • Organic Chemistry
    • Inorganic Chemistry

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