Direct and metal-free arylsulfonylation of alkynes with sulfonylhydrazides for the construction of 3-sulfonated coumarins

Chem Commun (Camb). 2015 Jan 14;51(4):768-71. doi: 10.1039/c4cc08117j.

Abstract

A novel and metal-free procedure has been developed for the construction of 3-sulfonated coumarins via the direct difunctionalization of alkynoates with sulfonylhydrazides. The present protocol, which simply utilizes TBAI as the catalyst and TBHP as the oxidant, provides a convenient and highly efficient approach to construct a series of sulfonated coumarins with high regioselectivity and good functional group tolerance.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Catalysis
  • Coumarins / chemical synthesis*
  • Coumarins / chemistry
  • Hydrazines / chemistry*
  • Oxidants / chemistry
  • Stereoisomerism
  • Sulfones / chemical synthesis*
  • Sulfones / chemistry

Substances

  • Alkynes
  • Coumarins
  • Hydrazines
  • Oxidants
  • Sulfones