Amide Iridium Complexes As Catalysts for Transfer Hydrogenation Reduction of N-sulfonylimine

J Org Chem. 2021 Mar 5;86(5):3850-3859. doi: 10.1021/acs.joc.0c02680. Epub 2021 Feb 17.

Abstract

Sulfonamide moieties widely exist in natural products, biologically active substance, and pharmaceuticals. Here, an efficient water-soluble amide iridium complexes-catalyzed transfer hydrogenation reduction of N-sulfonylimine is developed, which can be carried out under environmentally friendly conditions, affording a series of sulfonamide compounds in excellent yields (96-98%). In comparison with organic solvents, water is shown to be critical for a high catalytic transfer hydrogenation reduction in which the catalyst loading can be as low as 0.001 mol %. These amide iridium complexes are easy to synthesize, one structure of which was determined by single-crystal X-ray diffraction. This protocol gives an operationally simple, practical, and environmentally friendly strategy for synthesis of sulfonamide compounds.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides*
  • Catalysis
  • Hydrogenation
  • Imines
  • Iridium*
  • Sulfones

Substances

  • Amides
  • Imines
  • N-sulfonylimine
  • Sulfones
  • Iridium