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

Michael P. Cassidy, Jessica Raushel, Valery V. Fokin

Research output: Contribution to journal › Article

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

Fingerprint

Keywords

Alkynes
Azides
Copper
Oxidation
Synthetic methods

ASJC Scopus subject areas

Chemistry(all)

Cite this

Cassidy, M. P., Raushel, J., & Fokin, V. V. (2006). Practical synthesis of amides from in situ generated copper(I) acetylides and sulfonyl azides. Angewandte Chemie - International Edition, 45(19), 3154-3157. https://doi.org/10.1002/anie.200503805

@article{3da81e9236d2458894c95719288f765b,

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",

month = may,

day = "5",

doi = "10.1002/anie.200503805",

language = "English",

volume = "45",

pages = "3154--3157",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "19",

}

TY - JOUR

T1 - Practical synthesis of amides from in situ generated copper(I) acetylides and sulfonyl azides

AU - Cassidy, Michael P.

AU - Raushel, Jessica

AU - Fokin, Valery V.

PY - 2006/5/5

Y1 - 2006/5/5

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.

KW - Alkynes

KW - Azides

KW - Copper

KW - Oxidation

KW - Synthetic methods

UR - http://www.scopus.com/inward/record.url?scp=33746191914&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33746191914&partnerID=8YFLogxK

U2 - 10.1002/anie.200503805

DO - 10.1002/anie.200503805

M3 - Article

C2 - 16570330

AN - SCOPUS:33746191914

VL - 45

SP - 3154

EP - 3157

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 19

ER -

Access to Document

10.1002/anie.200503805