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

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

ASJC Scopus subject areas

Organic Chemistry
Physical and Theoretical Chemistry
Biochemistry

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10.1021/ol201949h

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

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.",

author = "Mikhail Zibinsky and Fokin, {Valery V.}",

year = "2011",

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day = "16",

doi = "10.1021/ol201949h",

language = "English",

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pages = "4870--4872",

journal = "Organic Letters",

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T1 - Reactivity of N-(1,2,4-triazolyl)-substituted 1,2,3-triazoles

AU - Zibinsky, Mikhail

AU - Fokin, Valery V.

PY - 2011/9/16

Y1 - 2011/9/16

N2 - 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.

AB - 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.

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

Abstract

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