A Family of Routes to Substituted Phenols, Including Meta-Substituted Phenols

• Author(s) / Creator(s)

  • Shao, Wenjie
  • Clive, Derrick L. J.

• A new family of routes to substituted phenols has been developed. 2-Bromo-3-
  methoxycyclohex-2-en-1-ones are readily deprotonated at C-6 and the resulting anions react
  smoothly with a variety of electrophiles; treatment with DBU in PhMe at room temperature then
  results in efficient aromatization to benzene derivatives of regiochemically defined substitution
  pattern. This sequence affords phenolic azides (ArN3), sulfides (ArSR, ArSAr'), selenides
  (ArSePh), alcohols [ArCH(OH)R], amino derivatives [ArCH(NHSO2Ar')R), and 1,2-
  benzenediols. A complementary set of substitution patterns is obtained by DIBAL-H reduction
  or reaction with a Grignard reagent before aromatization; the latter process gives compounds in
  which the newly-introduced substituent is meta to the phenolic hydroxyl.

• Date created

  2015-01-01

• Subjects / Keywords

  • Practical Synthesis
  • Thiosulfonates
  • Convenient
  • Olivetol
  • Reagent
  • Ethers
  • Acid

• Type of Item

  Article (Draft / Submitted)

• DOI

  https://doi.org/10.7939/r3-fbvm-7z62

• License

  This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright © 2015 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.5b02187.