TBAB-Catalyzed 1,6-Conjugate Sulfonylation of para-Quinone Methides: A Highly Efficient Approach to Unsymmetrical gem-Diarylmethyl Sulfones in Water

Molecules. 2020 Jan 26;25(3):539. doi: 10.3390/molecules25030539.

Abstract

A highly efficient sulfonylation of para-quinone methides with sulfonyl hydrazines in water has been developed on the basis of the mode involving a tetrabutyl ammonium bromide (TBAB)-promoted sulfa-1,6-conjugated addition pathway. This reaction provides a green and sustainable method to synthesize various unsymmetrical diarylmethyl sulfones, showing good functional group tolerance, scalability, and regioselectivity. Further transformation of the resulting diarylmethyl sulfones provides an efficient route to some functionalized molecules.

Keywords: green and sustainable chemistry; sulfa-1,6-conjugated addition; synthesis in water; unsymmetrical diarylmethyl sulfones.

MeSH terms

  • Catalysis
  • Indolequinones / chemistry*
  • Models, Molecular
  • Molecular Conformation
  • Molecular Structure
  • Quaternary Ammonium Compounds / chemistry*
  • Solvents
  • Sulfones / chemistry*
  • Temperature
  • Water / chemistry*

Substances

  • Indolequinones
  • Quaternary Ammonium Compounds
  • Solvents
  • Sulfones
  • Water
  • quinone methide
  • tetrabutylammonium