Indium-mediated cleavage of diphenyl diselenide and diphenyl disulfide: efficient one-pot synthesis of unsymmetrical diorganyl selenides, sulfides, and selenoesters

Wanida Munbunjong, Eun Hwa Lee, Poonlarp Ngernmaneerat, Sung Jun Kim, Gurpinder Singh, Warinthorn Chavasiri, Doo Ok Jang

Research output: Contribution to journalArticlepeer-review

32 Citations (Scopus)

Abstract

A convenient and efficient method was developed for the synthesis of alkyl phenyl selenides, sulfides, and selenoesters in one-pot reaction by using indium metal. The reaction showed the selectivity for tert-alkyl, benzylic, and allylic halides over primary and secondary alkyl halides. For the reaction of primary and secondary alkyl iodides and bromides, the yields of selenides were improved by the addition of a catalytic amount of iodine.

Original languageEnglish
Pages (from-to)2467-2471
Number of pages5
JournalTetrahedron
Volume65
Issue number12
DOIs
Publication statusPublished - 2009 Mar 21

Bibliographical note

Funding Information:
This work was supported by the Center for Bioactive Molecular Hybrids and Yonsei University. W.M. is thankful to Thailand Research Fund for the 2004 Royal Golden Jubilee Ph.D. research assistant fellowship.

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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