Palladium-catalyzed indolization of N-aroylbenzotriazoles with disubstituted alkynes

Itaru Nakamura, Tetsuya Nemoto, Naozumi Shiraiwa, Masahiro Terada

Research output: Contribution to journalArticlepeer-review

74 Citations (Scopus)

Abstract

The palladium-catalyzed denitrogenative indolization of N-aroylbenzotriazoles 1 and internal alkynes 2 produced the corresponding polysubstituted indoles 3 in good to high yields. For example, the reaction of 5,6-dimethyl-1-[4-(trifluoromethyl)benzoyl]benzotriazole (1j) with 6-dodecyne (2a), 4-octyne (2b), and diphenylacetylene (2f) in the presence of 10 mol % of Pd(PPh3)4 without solvent at 130 °C gave the corresponding indoles 3i, 3l, and 3p in 74, 71, and 41% yields, respectively. In the present reaction, the aroylbenzotriazole acts as a synthetic equivalent of a 2-haloanilide in Larock's indole synthesis.

Original languageEnglish
Pages (from-to)1055-1058
Number of pages4
JournalOrganic letters
Volume11
Issue number5
DOIs
Publication statusPublished - 2009 Mar 5

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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