Facile synthesis of dihaloheterocycles via electrophilic iodocyclization

Fan Yang, Tetsuo Kin, Ming Bao, Yoshinori Yamamoto

Research output: Contribution to journalArticle

41 Citations (Scopus)

Abstract

An efficient and facile electrophilic iodocyclization for the synthesis of various O-, N-, and S-containing dihaloheterocycles has been developed. A wide range of the substituted propargyl alcohols having -OH, -NTs, and -SAc functional groups reacted with molecular iodine or bromoiodine at ambient temperature to produce the corresponding dihalogenated O-, N-, and S-containing five- and six-membered heterocycles in good to high yields; Under optimized solvent conditions, the reactions of various substituted but-2-yn-1-ones bearing -OH, -NTs, and -SAc functional groups at C4-position, with iodine or bromoiodine at ambient temperature afforded the corresponding 3,4-diiodo- and 3-bromo-4-iodo-substituted furans, pyrroles, and thiophenes in good to high yields. Further transformation of the resulting iodine- or bromine-containing products to polyaromatics potentially of useful as organo-material intermediates has been investigated.

Original languageEnglish
Pages (from-to)10147-10155
Number of pages9
JournalTetrahedron
Volume67
Issue number52
DOIs
Publication statusPublished - 2011 Dec 30

Keywords

  • Dihaloheterocycles
  • Electrophilic iodocyclization
  • Iodine

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Facile synthesis of dihaloheterocycles via electrophilic iodocyclization'. Together they form a unique fingerprint.

  • Cite this