Simple sulfinate synthesis enables C-H trifluoromethylcyclopropanation

Angew Chem Int Ed Engl. 2014 Sep 8;53(37):9851-5. doi: 10.1002/anie.201406622. Epub 2014 Aug 3.

Abstract

A simple method to convert readily available carboxylic acids into sulfinate salts by employing an interrupted Barton decarboxylation reaction is reported. A medicinally oriented panel of ten new sulfinate reagents was created using this method, including a key trifluoromethylcyclopropanation reagent, TFCS-Na. The reactivity of six of these salts towards C-H functionalization was field-tested using several different classes of heterocycles.

Keywords: CH functionalization; analogue synthesis; bioisosteres; heterocycles; sulfinate salts.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acids, Heterocyclic
  • Catalysis
  • Models, Molecular
  • Molecular Structure
  • Sulfinic Acids / chemical synthesis*
  • Sulfinic Acids / chemistry*

Substances

  • Acids, Heterocyclic
  • Sulfinic Acids