Reaction condition controlled nickel(ii)-catalyzed C-C cross-coupling of alcohols

Meng Juan Zhang, Hong Xi Li, David J. Young, Hai Yan Li, Jian Ping Lang

    Research output: Contribution to journalArticlepeer-review

    Abstract

    The challenge in the C-C cross-coupling of secondary and primary alcohols using acceptorless dehydrogenation coupling (ADC) is the difficulty in accurately controlling product selectivities. Herein, we report a controlled approach to a diverse range of β-alkylated secondary alcohols, α-alkylated ketones and α,β-unsaturated ketones using the ADC methodology employing a Ni(ii) 4,6-dimethylpyrimidine-2-thiolate cluster catalyst under different reaction conditions. This catalyst could tolerate a wide range of substrates and exhibited a high activity for the annulation reaction of secondary alcohols with 2-aminobenzyl alcohols to yield quinolines. This work is an example of precise chemoselectivity control by careful choice of reaction conditions.

    Original languageEnglish
    Pages (from-to)3567-3574
    Number of pages8
    JournalOrganic and Biomolecular Chemistry
    Volume17
    Issue number14
    DOIs
    Publication statusPublished - 14 Apr 2019

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