One-Pot Synthesis of Aryl Selenonic Acids and Some Unexpected Byproducts

J Org Chem. 2021 Aug 6;86(15):9938-9944. doi: 10.1021/acs.joc.1c01369. Epub 2021 Jul 16.

Abstract

The synthesis of aryl selenonic acids was achieved from diverse aryl bromides via a one-pot method involving metalation, selenation, and oxidation with hydrogen peroxide followed by ion exchange to afford the pure products in 77-90% yield. An o-hydroxymethyl derivative was found to dehydrate readily, affording the first example of a cyclic selenonic ester, while two minor byproducts were isolated and shown by X-ray crystallography to be mixed salts of aryl selenonic acids with either the corresponding aryl seleninic or selenious acid.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bromides*
  • Oxidation-Reduction
  • Salts*

Substances

  • Bromides
  • Salts