Cationic Ir(I)-catalyzed sp3 C-H bond alkenylation of ureas with alkynes for the synthesis of 2,3-disubstituted indoles

Takanori Shibata, Hiroyuki Hirashima, Mitsugu Kasagawa, Kyoji Tsuchikama, Kohei Endo

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

Secondary sp3 C-H bond activation of ureas was achieved by a cationic Ir(I)-JOSIPHOS catalyst. Regioselective C-H bond cleavage adjacent to the nitrogen atom in N-benzylureas and an N-allyl urea possessing a 2-alkynylphenyl group, and subsequent intramolecular reaction with an alkyne along with double-bond isomerization provided 2,3-disubstituted indoles.

Original languageEnglish
Article numberU05011ST
Pages (from-to)2171-2176
Number of pages6
JournalSynlett
Issue number15
DOIs
Publication statusPublished - 2011 Aug 31

Keywords

  • C-H bond activation
  • directing group
  • indoles
  • iridium
  • ureas

ASJC Scopus subject areas

  • Organic Chemistry

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