Suzuki-Miyaura coupling with high turnover number using an N-acyl-N-heterocyclic carbene palladacycle precursor

Hector Palencia; Federico Garcia-Jimenez; James M. Takacs

doi:10.1016/j.tetlet.2004.03.138

Suzuki-Miyaura coupling with high turnover number using an N-acyl-N-heterocyclic carbene palladacycle precursor

Hector Palencia, Federico Garcia-Jimenez, James M. Takacs

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

56 Scopus citations

Abstract

A simple N-acylimidazolium salt precursor to a NHC-complexed palladacyclic ligand gives high turnover numbers (10⁷) for Suzuki-Miyaura coupling and is applied to the preparation of biaryls used in the synthesis of coumarins. The results suggest that N-acyl-NHC derivatives can contribute to further expanding the rich chemistry of NHCs.

Original language	English (US)
Pages (from-to)	3849-3853
Number of pages	5
Journal	Tetrahedron Letters
Volume	45
Issue number	20
DOIs	https://doi.org/10.1016/j.tetlet.2004.03.138
State	Published - May 10 2004

Keywords

Biaryls
Catalysis
Coumarin synthesis
N-Acyl-N-heterocyclic carbene
N-Heterocyclic carbene ligand
NHC
Palladium catalyst
Suzuki-Miyaura coupling

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2004.03.138

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title = "Suzuki-Miyaura coupling with high turnover number using an N-acyl-N-heterocyclic carbene palladacycle precursor",

abstract = "A simple N-acylimidazolium salt precursor to a NHC-complexed palladacyclic ligand gives high turnover numbers (107) for Suzuki-Miyaura coupling and is applied to the preparation of biaryls used in the synthesis of coumarins. The results suggest that N-acyl-NHC derivatives can contribute to further expanding the rich chemistry of NHCs.",

keywords = "Biaryls, Catalysis, Coumarin synthesis, N-Acyl-N-heterocyclic carbene, N-Heterocyclic carbene ligand, NHC, Palladium catalyst, Suzuki-Miyaura coupling",

author = "Hector Palencia and Federico Garcia-Jimenez and Takacs, {James M.}",

note = "Funding Information: Support from the University of Nebraska Research Initiative and the NSF (CHE-0316825) is gratefully acknowledged. The NMR spectrometers used were purchased with shared instrument funds (NIH SIG-1-510-RR-06307) and (NSF CHE-0091975, MRI-0079750). We thank Prof. Kevin Shaughnessy for a helpful discussion.",

year = "2004",

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doi = "10.1016/j.tetlet.2004.03.138",

language = "English (US)",

volume = "45",

pages = "3849--3853",

journal = "Tetrahedron Letters",

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T1 - Suzuki-Miyaura coupling with high turnover number using an N-acyl-N-heterocyclic carbene palladacycle precursor

AU - Palencia, Hector

AU - Garcia-Jimenez, Federico

AU - Takacs, James M.

N1 - Funding Information: Support from the University of Nebraska Research Initiative and the NSF (CHE-0316825) is gratefully acknowledged. The NMR spectrometers used were purchased with shared instrument funds (NIH SIG-1-510-RR-06307) and (NSF CHE-0091975, MRI-0079750). We thank Prof. Kevin Shaughnessy for a helpful discussion.

PY - 2004/5/10

Y1 - 2004/5/10

N2 - A simple N-acylimidazolium salt precursor to a NHC-complexed palladacyclic ligand gives high turnover numbers (107) for Suzuki-Miyaura coupling and is applied to the preparation of biaryls used in the synthesis of coumarins. The results suggest that N-acyl-NHC derivatives can contribute to further expanding the rich chemistry of NHCs.

AB - A simple N-acylimidazolium salt precursor to a NHC-complexed palladacyclic ligand gives high turnover numbers (107) for Suzuki-Miyaura coupling and is applied to the preparation of biaryls used in the synthesis of coumarins. The results suggest that N-acyl-NHC derivatives can contribute to further expanding the rich chemistry of NHCs.

KW - Biaryls

KW - Catalysis

KW - Coumarin synthesis

KW - N-Acyl-N-heterocyclic carbene

KW - N-Heterocyclic carbene ligand

KW - NHC

KW - Palladium catalyst

KW - Suzuki-Miyaura coupling

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DO - 10.1016/j.tetlet.2004.03.138

M3 - Article

AN - SCOPUS:1942532067

SN - 0040-4039

VL - 45

SP - 3849

EP - 3853

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 20

ER -

Suzuki-Miyaura coupling with high turnover number using an N-acyl-N-heterocyclic carbene palladacycle precursor

Abstract

Keywords

ASJC Scopus subject areas

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