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

• Author(s) / Creator(s)

  • Yu, Guojun
  • Clive, Derrick L. J.

• 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

  • Enantioselective TOtal-Synthesis
  • Magnetic-Resonance
  • Derivatives
  • Cyclohexenones
  • Cyclization
  • Reagents
  • Ring
  • PRecursosrs
  • Ethers
  • LICL

• 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.