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 journalArticle

3 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)3485-3491
Number of pages7
JournalAdvanced Synthesis and Catalysis
Volume355
Issue number17
DOIs
StatePublished - Nov 25 2013

Fingerprint

Rhodium
Addition reactions
phosphine
Alkynes
Dimerization
Metalloids
Electrons
Alkenes
Ketones
Catalysis
Olefins
Ligands
Catalysts
Metals
3-buten-2-one

Keywords

  • 1,4-addition
  • alkynes
  • enynes
  • multicomponent reactions
  • rhodium

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

A rhodium-catalyzed tandem alkyne dimerization/1,4-addition reaction. / Lerum, Ronald V.; Russo, Christopher M.; Marquez, Jocellie E.; Chisholm, John D.

In: Advanced Synthesis and Catalysis, Vol. 355, No. 17, 25.11.2013, p. 3485-3491.

Research output: Contribution to journalArticle

Lerum, Ronald V. ; Russo, Christopher M. ; Marquez, Jocellie E. ; Chisholm, John D. / A rhodium-catalyzed tandem alkyne dimerization/1,4-addition reaction. In: Advanced Synthesis and Catalysis. 2013 ; Vol. 355, No. 17. pp. 3485-3491.
@article{693c3c8bb37a44e59df49dc88fc87ef3,
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",
author = "Lerum, {Ronald V.} and Russo, {Christopher M.} and Marquez, {Jocellie E.} and Chisholm, {John D}",
year = "2013",
month = "11",
day = "25",
doi = "10.1002/adsc.201300743",
language = "English (US)",
volume = "355",
pages = "3485--3491",
journal = "Journal fur Praktische Chemie",
issn = "1436-9966",
publisher = "Wiley-VCH Verlag",
number = "17",

}

TY - JOUR

T1 - A rhodium-catalyzed tandem alkyne dimerization/1,4-addition reaction

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

UR - http://www.scopus.com/inward/record.url?scp=84888303916&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84888303916&partnerID=8YFLogxK

U2 - 10.1002/adsc.201300743

DO - 10.1002/adsc.201300743

M3 - Article

AN - SCOPUS:84888303916

VL - 355

SP - 3485

EP - 3491

JO - Journal fur Praktische Chemie

JF - Journal fur Praktische Chemie

SN - 1436-9966

IS - 17

ER -