Reactivity of N-(1,2,4-triazolyl)-substituted 1,2,3-triazoles

Mikhail Zibinsky, Valery V. Fokin

Research output: Contribution to journal › Article

55 Citations (Scopus)

Abstract

Synthetically useful rhodium(II) carbenes were obtained from N-(1,2,4-triazolyl)-substituted 1,2,3-triazoles and Rh(II) carboxylates. The electron-withdrawing 1,2,4-triazolyl group reveals the heretofore unknown reactivity of nonsulfonyl 1,2,3-triazoles, which exhibit the reactivity of diazo compounds. The resulting carbenes provide ready asymmetric access to secondary homoaminocyclopropanes (80-95% ee, dr >20:1) via reactions with olefins and also engage in efficient transannulation reactions with nitriles.

Original languageEnglish
Pages (from-to)4870-4872
Number of pages3
JournalOrganic Letters
Volume13
Issue number18
DOIs
Publication statusPublished - 16 Sep 2011
Externally publishedYes

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Triazoles
carbenes
reactivity
Nitriles
Rhodium
nitriles
Alkenes
rhodium
carboxylates
alkenes
Electrons
electrons
carbene

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Reactivity of N-(1,2,4-triazolyl)-substituted 1,2,3-triazoles. / Zibinsky, Mikhail; Fokin, Valery V.

In: Organic Letters, Vol. 13, No. 18, 16.09.2011, p. 4870-4872.

Research output: Contribution to journal › Article

Zibinsky, M & Fokin, VV 2011, 'Reactivity of N-(1,2,4-triazolyl)-substituted 1,2,3-triazoles', Organic Letters, vol. 13, no. 18, pp. 4870-4872. https://doi.org/10.1021/ol201949h
Zibinsky M, Fokin VV. Reactivity of N-(1,2,4-triazolyl)-substituted 1,2,3-triazoles. Organic Letters. 2011 Sep 16;13(18):4870-4872. https://doi.org/10.1021/ol201949h
Zibinsky, Mikhail ; Fokin, Valery V. / Reactivity of N-(1,2,4-triazolyl)-substituted 1,2,3-triazoles. In: Organic Letters. 2011 ; Vol. 13, No. 18. pp. 4870-4872.
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