Hypervalent Iodine Mediated Sulfonamide Synthesis

Diogo L. Poeira, João Macara, Hélio Faustino, Jaime A. S. Coelho, Pedro M. P. Gois, M. Manuel B. Marques

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

A new metal-free sulfonylation reaction is described. The method takes advantage of the Umpolung reactivity and group-transfer properties of iodine(III) compounds, combining hypervalent iodine reagents and sulfinate salts to deliver a clean and mild transfer of sulfonyl groups to amines and anilines. A total of 25 sulfonamides was synthesised in up to 99 % yield, even on gram-scale. The reaction mechanism was investigated by ESI-MS and DFT calculations.

Original languageEnglish
Pages (from-to)2695-2701
Number of pages7
JournalEuropean Journal of Organic Chemistry
Volume2019
Issue number15
DOIs
Publication statusPublished - 24 Apr 2019

Keywords

  • Hypervalent iodine
  • Sulfonamides
  • Synthetic methods
  • Umpolung

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