Mining the Chemical Space: Application of 2/4-Nitrobenzenesulfonamides in Solid-Phase Synthesis

ACS Comb Sci. 2015 Oct 12;17(10):570-91. doi: 10.1021/acscombsci.5b00089. Epub 2015 Sep 14.

Abstract

Polymer-supported benzenesulfonamides prepared from various immobilized primary amines and 2/4-nitrobenzenesulfonyl chloride have been used as key intermediates in different chemical transformations, including unusual rearrangements to yield a number of diverse privileged scaffolds. This review summarizes individual strategies in their application to date.

Keywords: 2-nitrobenzenesulfonyl chloride; 4-nitrobenzenesulfonyl chloride; C-arylation; Fukuyama alkylation; Fukuyama−Mitsunobu alkylation; N-arylation; protective group; rearrangement; solid-phase synthesis.

Publication types

  • Research Support, Non-U.S. Gov't
  • Review

MeSH terms

  • Amines / chemistry
  • Combinatorial Chemistry Techniques
  • Nitrobenzenes / chemical synthesis*
  • Nitrobenzenes / chemistry
  • Polymers / chemistry
  • Solid-Phase Synthesis Techniques / methods*
  • Sulfonamides / chemical synthesis*
  • Sulfonamides / chemistry

Substances

  • 4-nitrobenzenesulfonyl chloride
  • Amines
  • Nitrobenzenes
  • Polymers
  • Sulfonamides