Ir(III)-catalyzed C7-position-selective oxidative C -H alkenylation of indolines with alkenes in air

Shiguang Pan, Takayuki Wakaki, Naoto Ryu, Takanori Shibata

Research output: Contribution to journalArticle

47 Citations (Scopus)

Abstract

An efficient method for C7-position-selective alkenylation of N-substituted indolines with alkenes is reported. Various 7-alkenylindolines were obtained in moderate to excellent yields in air in the presence of catalytic amounts of [CpIrCl2]2, AgOTf, and Cu(OAc)2. The protocol relies on the use of a carbonyl or carbamoyl group on the nitrogen atom of indoline as a directing group and is potentially applicable to the synthesis of 7-alkenylindoles and 7-alkylindoles. Lettin the cat outta the bag: An efficient IrIII-catalyzed oxidative coupling of N-substituted indolines with various alkenes at the C7-position in air assisted by a carbonyl or carbamoyl group as a directing group is reported. The catalyst was prepared from [CpIrCl2]2 and AgOTf. A variety of 7-alkenylindolines were obtained in moderated to high yields. The reaction is potentially applicable to the synthesis of 7-alkylindoles and 7-alkenylindoles.

Original languageEnglish
Pages (from-to)1257-1260
Number of pages4
JournalChemistry - An Asian Journal
Volume9
Issue number5
DOIs
Publication statusPublished - 2014 May

Keywords

  • C-H activation
  • alkenes
  • alkenylation
  • indoline
  • iridium

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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