Skeletal rearrangement of cyano-substituted iminoisobenzofurans into alkyl 2-cyanobenzoates catalyzed by B(C6F5)3

Jing Li, Yasuhiro Okuda, Jiaji Zhao, Seiji Mori, Yasushi Nishihara

    Research output: Contribution to journalArticlepeer-review

    7 Citations (Scopus)

    Abstract

    An efficient method for the direct conversion of cyano-substituted iminoisobenzofurans into their corresponding alkyl 2-cyanobenzoates has been developed. This transformation proceeds via cleavage of C-C, C-O, and C-N bonds in starting iminoisobenzofurans. DFT study revealed that intermediate α-iminonitriles are produced in situ via C-C bond formation between 2-iminium benzoates and a cyanide ion. Generation of isocyanide as the byproduct in a more thermodynamic manner in DFT calculations also supports the experimental results.

    Original languageEnglish
    Pages (from-to)5220-5223
    Number of pages4
    JournalOrganic Letters
    Volume16
    Issue number19
    DOIs
    Publication statusPublished - Oct 3 2014

    ASJC Scopus subject areas

    • Biochemistry
    • Physical and Theoretical Chemistry
    • Organic Chemistry

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