The Suzuki-Miyaura reaction performed using a palladium-N-Heterocyclic carbene catalyst and a weak inorganic base

Frederic Izquierdo; Martin Michel Alfred Eton Corpet; Steven Patrick Nolan

doi:10.1002/ejoc.201500043

The Suzuki-Miyaura reaction performed using a palladium-N-Heterocyclic carbene catalyst and a weak inorganic base

Frederic Izquierdo, Martin Michel Alfred Eton Corpet, Steven Patrick Nolan

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

Abstract

N-Heterocyclic carbenes (NHCs) have been shown to be useful ligands for the Suzuki-Miyaura cross-coupling at low catalyst loadings. We now report that the commercially available and air-stable [Pd(IPr)(cin)Cl] pre-catalyst permits the formation of various functionalized biaryls from aryl chlorides and boronic acids (37 examples) under very mild conditions using a mixture of ethanol/water as solvent and an inorganic base.

Original language	English
Pages (from-to)	1920-1924
Number of pages	5
Journal	European Journal of Organic Chemistry
Early online date	18 Feb 2015
DOIs	https://doi.org/10.1002/ejoc.201500043
Publication status	Published - 2015

Keywords

Catalysis
Cross-coupling
NHC
Palladium
Suzuki-Miyaura

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10.1002/ejoc.201500043

Nolan_2015_EJOC_Suzuki_AM
Copyright © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This is the accepted version of the following article: Izquierdo, F., Corpet, M. and Nolan, S. P. (2015), The Suzuki–Miyaura Reaction Performed Using a Palladium–N-Heterocyclic Carbene Catalyst and a Weak Inorganic Base. Eur. J. Org. Chem., which has been published in final form at: http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201500043/abstract
Accepted author manuscript, 516 KB

Cite this

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title = "The Suzuki-Miyaura reaction performed using a palladium-N-Heterocyclic carbene catalyst and a weak inorganic base",

abstract = "N-Heterocyclic carbenes (NHCs) have been shown to be useful ligands for the Suzuki-Miyaura cross-coupling at low catalyst loadings. We now report that the commercially available and air-stable [Pd(IPr)(cin)Cl] pre-catalyst permits the formation of various functionalized biaryls from aryl chlorides and boronic acids (37 examples) under very mild conditions using a mixture of ethanol/water as solvent and an inorganic base.",

keywords = "Catalysis, Cross-coupling, NHC, Palladium, Suzuki-Miyaura",

author = "Frederic Izquierdo and Corpet, \{Martin Michel Alfred Eton\} and Nolan, \{Steven Patrick\}",

note = "We gratefully acknowledge the EC for funding through the seventh framework program SYNFLOW, the ERC (Advanced Investigator Award {\textquoteleft}FUNCAT{\textquoteright} to SPN) and the EPSRC. S.P.N. is a Royal Society Wolfson Research Merit Award holder.",

year = "2015",

doi = "10.1002/ejoc.201500043",

language = "English",

pages = "1920--1924",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH, Weinheim",

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T1 - The Suzuki-Miyaura reaction performed using a palladium-N-Heterocyclic carbene catalyst and a weak inorganic base

AU - Izquierdo, Frederic

AU - Corpet, Martin Michel Alfred Eton

AU - Nolan, Steven Patrick

N1 - We gratefully acknowledge the EC for funding through the seventh framework program SYNFLOW, the ERC (Advanced Investigator Award ‘FUNCAT’ to SPN) and the EPSRC. S.P.N. is a Royal Society Wolfson Research Merit Award holder.

PY - 2015

Y1 - 2015

N2 - N-Heterocyclic carbenes (NHCs) have been shown to be useful ligands for the Suzuki-Miyaura cross-coupling at low catalyst loadings. We now report that the commercially available and air-stable [Pd(IPr)(cin)Cl] pre-catalyst permits the formation of various functionalized biaryls from aryl chlorides and boronic acids (37 examples) under very mild conditions using a mixture of ethanol/water as solvent and an inorganic base.

AB - N-Heterocyclic carbenes (NHCs) have been shown to be useful ligands for the Suzuki-Miyaura cross-coupling at low catalyst loadings. We now report that the commercially available and air-stable [Pd(IPr)(cin)Cl] pre-catalyst permits the formation of various functionalized biaryls from aryl chlorides and boronic acids (37 examples) under very mild conditions using a mixture of ethanol/water as solvent and an inorganic base.

KW - Catalysis

KW - Cross-coupling

KW - NHC

KW - Palladium

KW - Suzuki-Miyaura

UR - http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201500043/suppinfo

UR - https://www.scopus.com/pages/publications/85027927482

U2 - 10.1002/ejoc.201500043

DO - 10.1002/ejoc.201500043

M3 - Article

SN - 1434-193X

SP - 1920

EP - 1924

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

ER -

The Suzuki-Miyaura reaction performed using a palladium-N-Heterocyclic carbene catalyst and a weak inorganic base

Abstract

Keywords

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LSI Collaborative Project: SYNFLOW: EU FP7 Collaborative Project 'SYNFLOW'

FUNCAT: EU FP7 ERC Advanced Grant - FUNCAT - Fundamental Studies in Organometallic Chemistry and Homogeneous Catalysis

N-heterocyclic carbenes in palladium-catalysed cross-coupling reactions

Cite this

The Suzuki-Miyaura reaction performed using a palladium-N-Heterocyclic carbene catalyst and a weak inorganic base

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Projects

LSI Collaborative Project: SYNFLOW: EU FP7 Collaborative Project 'SYNFLOW'

FUNCAT: EU FP7 ERC Advanced Grant - FUNCAT - Fundamental Studies in Organometallic Chemistry and Homogeneous Catalysis

Student theses

N-heterocyclic carbenes in palladium-catalysed cross-coupling reactions

Cite this