A rhodium-catalyzed tandem alkyne dimerization/1,4-addition reaction

Ronald V. Lerum; Christopher M. Russo; Jocellie E. Marquez; John D. Chisholm

doi:10.1002/adsc.201300743

A rhodium-catalyzed tandem alkyne dimerization/1,4-addition reaction

Ronald V. Lerum, Christopher M. Russo, Jocellie E. Marquez, John D. Chisholm

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

4 Scopus citations

Abstract

A convenient three-component coupling reaction for the construction of conjugated enynes using rhodium catalysis is reported. Dimerization of a monosubstituted alkyne followed by trapping of the vinyl metal intermediate with an electron-deficient alkene, such as methyl vinyl ketone, provided moderate to good yields of these enynes. The use of the hindered electron-rich tris(ortho-tolyl)phosphine as a ligand for the rhodium catalyst provided the best conversions to these complex products.

Original language	English (US)
Pages (from-to)	3485-3491
Number of pages	7
Journal	Advanced Synthesis and Catalysis
Volume	355
Issue number	17
DOIs	https://doi.org/10.1002/adsc.201300743
State	Published - Nov 25 2013

Keywords

1,4-addition
alkynes
enynes
multicomponent reactions
rhodium

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.201300743

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title = "A rhodium-catalyzed tandem alkyne dimerization/1,4-addition reaction",

abstract = "A convenient three-component coupling reaction for the construction of conjugated enynes using rhodium catalysis is reported. Dimerization of a monosubstituted alkyne followed by trapping of the vinyl metal intermediate with an electron-deficient alkene, such as methyl vinyl ketone, provided moderate to good yields of these enynes. The use of the hindered electron-rich tris(ortho-tolyl)phosphine as a ligand for the rhodium catalyst provided the best conversions to these complex products.",

keywords = "1,4-addition, alkynes, enynes, multicomponent reactions, rhodium",

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AU - Lerum, Ronald V.

AU - Russo, Christopher M.

AU - Marquez, Jocellie E.

AU - Chisholm, John D.

PY - 2013/11/25

Y1 - 2013/11/25

N2 - A convenient three-component coupling reaction for the construction of conjugated enynes using rhodium catalysis is reported. Dimerization of a monosubstituted alkyne followed by trapping of the vinyl metal intermediate with an electron-deficient alkene, such as methyl vinyl ketone, provided moderate to good yields of these enynes. The use of the hindered electron-rich tris(ortho-tolyl)phosphine as a ligand for the rhodium catalyst provided the best conversions to these complex products.

AB - A convenient three-component coupling reaction for the construction of conjugated enynes using rhodium catalysis is reported. Dimerization of a monosubstituted alkyne followed by trapping of the vinyl metal intermediate with an electron-deficient alkene, such as methyl vinyl ketone, provided moderate to good yields of these enynes. The use of the hindered electron-rich tris(ortho-tolyl)phosphine as a ligand for the rhodium catalyst provided the best conversions to these complex products.

KW - 1,4-addition

KW - alkynes

KW - enynes

KW - multicomponent reactions

KW - rhodium

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JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 17

ER -

A rhodium-catalyzed tandem alkyne dimerization/1,4-addition reaction

Abstract

Keywords

ASJC Scopus subject areas

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