Photocatalyzed Site-Selective C(sp3)-H Functionalization of Alkylpyridines at Non-Benzylic Positions

Takahide Fukuyama, Tomohiro Nishikawa, Keiichi Yamada, Davide Ravelli, Maurizio Fagnoni, Ilhyong Ryu*

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    21 Scopus citations

    Abstract

    Tetrabutylammonium decatungstate (TBADT)-photocatalyzed C-H functionalization of alkylpyridines was investigated. Unlike alkylbenzene counterparts, alkylation of α-C-H bonds did not proceed for the reaction of 2- and 4-alkylpyridines and reluctantly proceeded for 3-alkylpyridines, which allow site-selective C(sp3)-H functionalization at nonbenzylic positions. The observed nonbenzylic site selectivities are rationalized by the polar inductive effects of pyridyl groups in the SH2 transition states. Consecutive γ-functionalization and α-bromofunctionalization were successfully carried out in selected cases.

    Original languageEnglish
    Pages (from-to)6436-6439
    Number of pages4
    JournalOrganic Letters
    Volume19
    Issue number23
    DOIs
    StatePublished - 1 Dec 2017

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