Double duty for cyanogen bromide in a cascade synthesis of cyanoepoxides

Zhou Li; Vladimir Gevorgyan

doi:10.1002/anie.201006966

Double duty for cyanogen bromide in a cascade synthesis of cyanoepoxides

Zhou Li, Vladimir Gevorgyan

Research output: Contribution to journal › Article › peer-review

21 Scopus citations

Abstract

An unprecedented reaction mode of cyanogen bromide has been discovered. Under basic conditions, cyanogen bromide acts as an equivalent of both Br ⁺ and CN^- to convert enolizable ketones into the corresponding cyanoepoxides in good yields. This unique reaction mode provides new, one-pot access to densely substituted cyanoepoxides from easily available ketones (see scheme).

Original language	English (US)
Pages (from-to)	2808-2810
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	50
Issue number	12
DOIs	https://doi.org/10.1002/anie.201006966
State	Published - Mar 14 2011
Externally published	Yes

Keywords

cascade reactions
cyanoepoxides
cyanogen bromide
synthetic methods

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.201006966

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abstract = "An unprecedented reaction mode of cyanogen bromide has been discovered. Under basic conditions, cyanogen bromide acts as an equivalent of both Br + and CN- to convert enolizable ketones into the corresponding cyanoepoxides in good yields. This unique reaction mode provides new, one-pot access to densely substituted cyanoepoxides from easily available ketones (see scheme).",

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author = "Zhou Li and Vladimir Gevorgyan",

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AU - Gevorgyan, Vladimir

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AB - An unprecedented reaction mode of cyanogen bromide has been discovered. Under basic conditions, cyanogen bromide acts as an equivalent of both Br + and CN- to convert enolizable ketones into the corresponding cyanoepoxides in good yields. This unique reaction mode provides new, one-pot access to densely substituted cyanoepoxides from easily available ketones (see scheme).

KW - cascade reactions

KW - cyanoepoxides

KW - cyanogen bromide

KW - synthetic methods

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Double duty for cyanogen bromide in a cascade synthesis of cyanoepoxides

Abstract

Keywords

ASJC Scopus subject areas

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