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Iron-Facilitated Iodine-Mediated Electrophilic Annulation of N,N-Dimethyl-2-alkynylanilines with Disulfides or Diselenides

✍ Scribed by Hui-Ai Du; Ri-Yuan Tang; Chen-Liang Deng; Yan Liu; Jin-Heng Li; Xing-Guo Zhang

Publisher
John Wiley and Sons
Year
2011
Tongue
English
Weight
249 KB
Volume
353
Category
Article
ISSN
1615-4150

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✦ Synopsis

Abstract

An efficient synthesis of N‐methyl‐3‐chalcogeno‐indoles has been developed via iodine‐mediated electrophilic annulation reactions of 2‐alkynylaniline derivatives with disulfides or diselenides. In the presence of iodine and iron, a variety of 2‐alkynylanilines selectively underwent the electrophilic annulation with numerous disulfides or diselenides leading to the corresponding 3‐sulfenylindoles and 3‐selenenylindoles in moderate to excellent yields. It is noteworthy that iron can promote the reaction.

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