Practical synthesis of amides from in situ generated copper(I) acetylides and sulfonyl azides

Abstract

(Chemical Equation Presented) A direct, simple, and efficient route from terminal alkynes to amides is achieved by their copper(I)-catalyzed reaction with sulfonyl azides (see scheme). The reaction proceeds with the in situ generation of copper(I) acetylides and represents a one-step formal oxidative hydration of a triple bond.

Original language	English
Pages (from-to)	3154-3157
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	45
Issue number	19
DOIs	https://doi.org/10.1002/anie.200503805
Publication status	Published - 5 May 2006
Externally published	Yes

Keywords

Alkynes
Azides
Copper
Oxidation
Synthetic methods

ASJC Scopus subject areas

Chemistry(all)

Access to Document

10.1002/anie.200503805

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title = "Practical synthesis of amides from in situ generated copper(I) acetylides and sulfonyl azides",

abstract = "(Chemical Equation Presented) A direct, simple, and efficient route from terminal alkynes to amides is achieved by their copper(I)-catalyzed reaction with sulfonyl azides (see scheme). The reaction proceeds with the in situ generation of copper(I) acetylides and represents a one-step formal oxidative hydration of a triple bond.",

keywords = "Alkynes, Azides, Copper, Oxidation, Synthetic methods",

author = "Cassidy, {Michael P.} and Jessica Raushel and Fokin, {Valery V.}",

year = "2006",

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AU - Fokin, Valery V.

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N2 - (Chemical Equation Presented) A direct, simple, and efficient route from terminal alkynes to amides is achieved by their copper(I)-catalyzed reaction with sulfonyl azides (see scheme). The reaction proceeds with the in situ generation of copper(I) acetylides and represents a one-step formal oxidative hydration of a triple bond.

AB - (Chemical Equation Presented) A direct, simple, and efficient route from terminal alkynes to amides is achieved by their copper(I)-catalyzed reaction with sulfonyl azides (see scheme). The reaction proceeds with the in situ generation of copper(I) acetylides and represents a one-step formal oxidative hydration of a triple bond.

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KW - Azides

KW - Copper

KW - Oxidation

KW - Synthetic methods

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