Arylation of ortho-Hydroxyarylenaminones by Sulfonium Salts and Arenesulfonyl Chlorides: An Access to Isoflavones

J Org Chem. 2021 Apr 2;86(7):4896-4916. doi: 10.1021/acs.joc.0c02294. Epub 2021 Mar 15.

Abstract

Herein we disclose three new methods for the straightforward and efficient synthesis of 3-arylchromones following the arylation of ortho-hydroxyarylenaminones by vast diversities of bench-stable and easy-to-use sulfonium salts and arenesulfonyl chlorides. Both developed methods, namely the light-mediated photoredox and electrophilic arylation, showed good efficiency, and are feasible for the preparation of 3-arylchromones in good-to-excellent yields. This work showcases the first described attempt where the sulfonium salts and arenesulfonyl chlorides were successfully utilized for the construction of the chromone heterocycle system.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chlorides
  • Chromones
  • Isoflavones*
  • Salts*

Substances

  • Chlorides
  • Chromones
  • Isoflavones
  • Salts