Formation of 3-Aminophenols from Cyclohexane-1,3-diones.

• Author(s) / Creator(s)

  • Szymor-Pietrzak, Damian
  • Khan, Muhammad N.
  • Pagès, Anaïs
  • Kumar, Ajay
  • Depner, Noah
  • Clive, Derrick L. J.

• meta-Aminophenols are formed by the action of DBU on 3-amino-2-chlorocyclohex-2-en-1-ones
  at room temperature in MeCN. The chloro compounds are generated by treating 3-
  aminocyclohex-2-en-1-ones with the easily prepared halogenating agent BnNMe3.ICl2 in MeOHCH2Cl2.
  The amino group must carry two substituents, either two aryl, one aryl and one alkyl or
  two alkyl groups; 3-aminocyclohex-2-en-1-ones of this type are readily made from cyclohex-2-
  en-1-one and a primary or secondary amine.

• Date created

  2021-01-01

• Subjects / Keywords

  • Palladium-Catalyzed Synthesis
  • Exocyclic Beta-Enaminones
  • Reductive Amination
  • Ytterbium-Triflate
  • One-Pot
  • Aromatization
  • Halogenation
  • Efficient
  • Phenols
  • Alkaloids

• Type of Item

  Article (Draft / Submitted)

• DOI

  https://doi.org/10.7939/r3-j0dy-ny53

• License

  This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright © 2020 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.0c02284.