An efficient, facile, and general synthesis of 1H-indazoles by 1,3-dipolar cycloaddition of arynes with diazomethane derivatives

Tienan Jin, Yoshinori Yamamoto

Research output: Contribution to journalArticle

124 Citations (Scopus)

Abstract

(Chemical Equation Presented) Take your pick: Both N-unsubstituted and 1-aryl 1H-indazoles are available in good to high yields through the [3+2] cycloaddition of benzynes derived from o-silylaryl triflates with diazomethane derivatives (see scheme). In the presence of KF/[18]crown-6, the N-unsubstituted 1H-indazole is formed, whereas the 1-arylated product is obtained regioselectively with CsF and an excess of the triflate.

Original languageEnglish
Pages (from-to)3323-3325
Number of pages3
JournalAngewandte Chemie - International Edition
Volume46
Issue number18
DOIs
Publication statusPublished - 2007 Jun 29

Keywords

  • 1,3-dipolar cycloaddition
  • Arynes
  • Diazo compounds
  • Heterocycles
  • Indazoles

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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