Iron-catalyzed directed C2-alkylation and alkenylation of indole with vinylarenes and alkynes

Mun Yee Wong, Takeshi Yamakawa, Naohiko Yoshikai

Research output: Contribution to journalArticlepeer-review

73 Citations (Scopus)

Abstract

An iron-N-heterocyclic carbene catalyst generated from an iron(III) salt, an imidazolinium salt, and a Grignard reagent promotes alkylation and alkenylation reactions at the indole C2-position with vinylarenes and internal alkynes, respectively, via imine-directed C-H activation. The former reaction affords 1,1-diarylalkane derivatives with exclusive regioselectivity. Deuterium-labeling experiments suggest that these reactions involve oxidative addition of the C-H bond to the iron center, insertion of the unsaturated bond into the Fe-H bond, and C-C reductive elimination.

Original languageEnglish
Pages (from-to)442-445
Number of pages4
JournalOrganic letters
Volume17
Issue number3
DOIs
Publication statusPublished - 2015 Feb 6
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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