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

Mikhail Zibinsky, Valery V. Fokin

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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 language	English
Pages (from-to)	4870-4872
Number of pages	3
Journal	Organic Letters
Volume	13
Issue number	18
DOIs	https://doi.org/10.1021/ol201949h
Publication status	Published - 16 Sep 2011
Externally published	Yes

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ASJC Scopus subject areas

Organic Chemistry
Physical and Theoretical Chemistry
Biochemistry

Cite this

Zibinsky, M., & Fokin, V. V. (2011). Reactivity of N-(1,2,4-triazolyl)-substituted 1,2,3-triazoles. Organic Letters, 13(18), 4870-4872. https://doi.org/10.1021/ol201949h

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Access to Document

10.1021/ol201949h