Copper-carbene complexes as catalysts in the synthesis of functionalized styrenes and aliphatic alkenes

Helene Lebel; Michael Davi; Silvia Diez-Gonzalez; Steven Patrick Nolan

doi:10.1021/jo061781a

Copper-carbene complexes as catalysts in the synthesis of functionalized styrenes and aliphatic alkenes

Helene Lebel, Michael Davi, Silvia Diez-Gonzalez, Steven Patrick Nolan

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

Abstract

[GRAPHICS]

(NHC) -Cu (NHC= N-heterocyclic carbene) complexes efficiently catalyzed the methylenation of a variety of aliphatic and aromatic aldehydes and ketones in the presence of trimethylsilyldiazomethane, triphenylphosphine, and 2-propanol. The copper catalysts are not only inexpensive compared to rhodium complexes, but they also exhibit better functional group compatibility with aromatic aldehydes and ketones. Indeed very high yields were obtained for the formation of styrenes containing nitro, trifluoromethyl, amino, and ester groups, as well as for pyridine-, pyrrole-, and indole-substituted alkenes.

Original language	English
Pages (from-to)	144-149
Number of pages	6
Journal	The Journal of Organic Chemistry
Volume	72
Issue number	1
DOIs	https://doi.org/10.1021/jo061781a
Publication status	Published - 5 Jan 2007

Keywords

N-HETEROCYCLIC CARBENE
ALDEHYDE-OLEFINATION CATALYSTS
MAIN-GROUP ELEMENTS
ALKOXY-NHC LIGANDS
ETHYL DIAZOACETATE
CARBONYL-COMPOUNDS
CONJUGATE ADDITION
PORPHYRIN COMPLEX
SELECTIVE OLEFINATION
TRANSITION-METALS

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10.1021/jo061781a

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title = "Copper-carbene complexes as catalysts in the synthesis of functionalized styrenes and aliphatic alkenes",

abstract = "[GRAPHICS](NHC) -Cu (NHC= N-heterocyclic carbene) complexes efficiently catalyzed the methylenation of a variety of aliphatic and aromatic aldehydes and ketones in the presence of trimethylsilyldiazomethane, triphenylphosphine, and 2-propanol. The copper catalysts are not only inexpensive compared to rhodium complexes, but they also exhibit better functional group compatibility with aromatic aldehydes and ketones. Indeed very high yields were obtained for the formation of styrenes containing nitro, trifluoromethyl, amino, and ester groups, as well as for pyridine-, pyrrole-, and indole-substituted alkenes.",

keywords = "N-HETEROCYCLIC CARBENE, ALDEHYDE-OLEFINATION CATALYSTS, MAIN-GROUP ELEMENTS, ALKOXY-NHC LIGANDS, ETHYL DIAZOACETATE, CARBONYL-COMPOUNDS, CONJUGATE ADDITION, PORPHYRIN COMPLEX, SELECTIVE OLEFINATION, TRANSITION-METALS",

author = "Helene Lebel and Michael Davi and Silvia Diez-Gonzalez and Nolan, {Steven Patrick}",

year = "2007",

month = jan,

day = "5",

doi = "10.1021/jo061781a",

language = "English",

volume = "72",

pages = "144--149",

journal = "The Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society (ACS)",

number = "1",

}

TY - JOUR

T1 - Copper-carbene complexes as catalysts in the synthesis of functionalized styrenes and aliphatic alkenes

AU - Lebel, Helene

AU - Davi, Michael

AU - Diez-Gonzalez, Silvia

AU - Nolan, Steven Patrick

PY - 2007/1/5

Y1 - 2007/1/5

N2 - [GRAPHICS](NHC) -Cu (NHC= N-heterocyclic carbene) complexes efficiently catalyzed the methylenation of a variety of aliphatic and aromatic aldehydes and ketones in the presence of trimethylsilyldiazomethane, triphenylphosphine, and 2-propanol. The copper catalysts are not only inexpensive compared to rhodium complexes, but they also exhibit better functional group compatibility with aromatic aldehydes and ketones. Indeed very high yields were obtained for the formation of styrenes containing nitro, trifluoromethyl, amino, and ester groups, as well as for pyridine-, pyrrole-, and indole-substituted alkenes.

AB - [GRAPHICS](NHC) -Cu (NHC= N-heterocyclic carbene) complexes efficiently catalyzed the methylenation of a variety of aliphatic and aromatic aldehydes and ketones in the presence of trimethylsilyldiazomethane, triphenylphosphine, and 2-propanol. The copper catalysts are not only inexpensive compared to rhodium complexes, but they also exhibit better functional group compatibility with aromatic aldehydes and ketones. Indeed very high yields were obtained for the formation of styrenes containing nitro, trifluoromethyl, amino, and ester groups, as well as for pyridine-, pyrrole-, and indole-substituted alkenes.

KW - N-HETEROCYCLIC CARBENE

KW - ALDEHYDE-OLEFINATION CATALYSTS

KW - MAIN-GROUP ELEMENTS

KW - ALKOXY-NHC LIGANDS

KW - ETHYL DIAZOACETATE

KW - CARBONYL-COMPOUNDS

KW - CONJUGATE ADDITION

KW - PORPHYRIN COMPLEX

KW - SELECTIVE OLEFINATION

KW - TRANSITION-METALS

UR - http://www.scopus.com/inward/record.url?scp=33846081585&partnerID=8YFLogxK

U2 - 10.1021/jo061781a

DO - 10.1021/jo061781a

M3 - Article

SN - 0022-3263

VL - 72

SP - 144

EP - 149

JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

IS - 1

ER -

Copper-carbene complexes as catalysts in the synthesis of functionalized styrenes and aliphatic alkenes

Abstract

Keywords

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