Rhodium-catalyzed 1,4-addition of terminal alkynes to vinyl ketones

Ronald V. Lerum; John D. Chisholm

doi:10.1016/j.tetlet.2004.07.036

Rhodium-catalyzed 1,4-addition of terminal alkynes to vinyl ketones

Ronald V. Lerum, John D. Chisholm

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

52 Scopus citations

Abstract

The metal complex Rh(acac)(CO) ₂ in the presence of an eqimolar amount of tris(o-methoxyphenyl)phosphine provides a useful catalyst system for the 1,4-addition of alkynes to unsubstituted vinyl ketones. Best yields are obtained when the transformation is performed in benzene at reflux with an excess of vinyl ketone. Both aryl and alkyl substituted alkynes participate in the reaction. Primary alcohols and alkyl chlorides are well tolerated under these reaction conditions. The reaction also proceeds in aqueous solvent mixtures, unlike most organometallic addition reactions.

Original language	English (US)
Pages (from-to)	6591-6594
Number of pages	4
Journal	Tetrahedron Letters
Volume	45
Issue number	35
DOIs	https://doi.org/10.1016/j.tetlet.2004.07.036
State	Published - Aug 23 2004

Keywords

1,4-Addition
Alkyne
Rhodium

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2004.07.036

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title = "Rhodium-catalyzed 1,4-addition of terminal alkynes to vinyl ketones",

abstract = "The metal complex Rh(acac)(CO) 2 in the presence of an eqimolar amount of tris(o-methoxyphenyl)phosphine provides a useful catalyst system for the 1,4-addition of alkynes to unsubstituted vinyl ketones. Best yields are obtained when the transformation is performed in benzene at reflux with an excess of vinyl ketone. Both aryl and alkyl substituted alkynes participate in the reaction. Primary alcohols and alkyl chlorides are well tolerated under these reaction conditions. The reaction also proceeds in aqueous solvent mixtures, unlike most organometallic addition reactions.",

keywords = "1,4-Addition, Alkyne, Rhodium",

author = "Lerum, {Ronald V.} and Chisholm, {John D.}",

note = "Funding Information: Acknowledgment is made to the Donors of the American Chemical Society Petroleum Research Fund and to Syracuse University for partial support of this research. Copyright: Copyright 2012 Elsevier B.V., All rights reserved.",

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AU - Lerum, Ronald V.

AU - Chisholm, John D.

N1 - Funding Information: Acknowledgment is made to the Donors of the American Chemical Society Petroleum Research Fund and to Syracuse University for partial support of this research. Copyright: Copyright 2012 Elsevier B.V., All rights reserved.

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Y1 - 2004/8/23

N2 - The metal complex Rh(acac)(CO) 2 in the presence of an eqimolar amount of tris(o-methoxyphenyl)phosphine provides a useful catalyst system for the 1,4-addition of alkynes to unsubstituted vinyl ketones. Best yields are obtained when the transformation is performed in benzene at reflux with an excess of vinyl ketone. Both aryl and alkyl substituted alkynes participate in the reaction. Primary alcohols and alkyl chlorides are well tolerated under these reaction conditions. The reaction also proceeds in aqueous solvent mixtures, unlike most organometallic addition reactions.

AB - The metal complex Rh(acac)(CO) 2 in the presence of an eqimolar amount of tris(o-methoxyphenyl)phosphine provides a useful catalyst system for the 1,4-addition of alkynes to unsubstituted vinyl ketones. Best yields are obtained when the transformation is performed in benzene at reflux with an excess of vinyl ketone. Both aryl and alkyl substituted alkynes participate in the reaction. Primary alcohols and alkyl chlorides are well tolerated under these reaction conditions. The reaction also proceeds in aqueous solvent mixtures, unlike most organometallic addition reactions.

KW - 1,4-Addition

KW - Alkyne

KW - Rhodium

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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Rhodium-catalyzed 1,4-addition of terminal alkynes to vinyl ketones

Abstract

Keywords

ASJC Scopus subject areas

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