Benzothiazole Sulfinate: A Sulfinic Acid Transfer Reagent under Oxidation-Free Conditions

Org Lett. 2017 Jul 21;19(14):3819-3822. doi: 10.1021/acs.orglett.7b01693. Epub 2017 Jul 3.

Abstract

Sulfinic acids are commonly encountered intermediates found in natural product synthesis and medicinal chemistry. However, because of high reactivity, instability, and harsh reaction conditions, they are difficult to synthesize. Herein we have developed an oxidation-free method to produce sulfinic acids and sulfinate salts using 2-sulfinyl benzothiazole (BTS). We have also demonstrated the synthetic usefulness by developing one-pot syntheses of sulfones and sulfonamides.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Benzothiazoles / chemistry*
  • Indicators and Reagents
  • Molecular Structure
  • Oxidation-Reduction
  • Sulfinic Acids

Substances

  • Benzothiazoles
  • Indicators and Reagents
  • Sulfinic Acids