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Formation of meta-Substituted Phenols by Transition Metal-Free Aromatization: Use of 2-Bromocyclohex-2-en-1-ones.

  • Author(s) / Creator(s)
  • Addition of Grignard- or other organometallic reagents to 3-halocyclohex-2-en-
    1-ones bearing an alkyl or aryl group at C-5, followed by mild acid treatment and exposure to
    DBU at room temperature, generates meta-substituted phenols in which the newly introduced
    meta substituent originates from the Grignard reagent. The range of effective organometallic
    reagents includes alkyl, allyl, alkynyl, aryl and heteroaryl compounds including those with
    fluorine substituents. The initial halocyclohexenone can be deprotonated at C-6 and reacted with
    carbon, fluorine or sulfur electrophiles before the Grignard addition so as to generate highly
    substituted phenols.

  • Date created
    2016-01-01
  • Subjects / Keywords
  • Type of Item
    Article (Draft / Submitted)
  • DOI
    https://doi.org/10.7939/r3-jesq-g504
  • License
    This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright © 2016 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.6b01653.
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  • Citation for previous publication
    • Yu, G., & Clive, D. L. J. (2016). Formation of meta-Substituted Phenols by Transition Metal-Free Aromatization: Use of 2-Bromocyclohex-2-en-1-ones. Journal of Organic Chemistry, 81(18), 8470–8484. https://doi-org.login.ezproxy.library.ualberta.ca/10.1021/acs.joc.6b01653