Room-temperature synthesis of tetra-ortho-substituted biaryls by NHC-catalyzed Suzuki-Miyaura couplings

Linglin Wu; Emma Drinkel; Fiona Gaggia; Samanta Capolicchio; Anthony Linden; Laura Falivene; Luigi Cavallo; Reto Dorta

doi:10.1002/chem.201102442

Room-temperature synthesis of tetra-ortho-substituted biaryls by NHC-catalyzed Suzuki-Miyaura couplings

Linglin Wu, Emma Drinkel, Fiona Gaggia, Samanta Capolicchio, Anthony Linden, Laura Falivene, Luigi Cavallo, Reto Dorta^*

^*Corresponding author for this work

Physical Sciences and Engineering

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

87 Scopus citations

Abstract

Into the groove: The introduction of a C ₂-symmetric N-heterocyclic carbene ligand with appropriately substituted naphthyl side chains enables the efficient Suzuki-Miyaura coupling to form bulky tetra-ortho-substituted biaryls from aryl bromides and chlorides at room temperature. DFT calculations uncover the subtle steric phenomena at play that lead to the superior catalytic performance. Cyoct=cyclooctyl.

Original language	English (US)
Pages (from-to)	12886-12890
Number of pages	5
Journal	Chemistry - A European Journal
Volume	17
Issue number	46
DOIs	https://doi.org/10.1002/chem.201102442
State	Published - Nov 11 2011

Keywords

N-heterocyclic carbene ligand
biaryls
cross-coupling
palladium

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.201102442

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abstract = "Into the groove: The introduction of a C 2-symmetric N-heterocyclic carbene ligand with appropriately substituted naphthyl side chains enables the efficient Suzuki-Miyaura coupling to form bulky tetra-ortho-substituted biaryls from aryl bromides and chlorides at room temperature. DFT calculations uncover the subtle steric phenomena at play that lead to the superior catalytic performance. Cyoct=cyclooctyl.",

keywords = "N-heterocyclic carbene ligand, biaryls, cross-coupling, palladium",

author = "Linglin Wu and Emma Drinkel and Fiona Gaggia and Samanta Capolicchio and Anthony Linden and Laura Falivene and Luigi Cavallo and Reto Dorta",

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T1 - Room-temperature synthesis of tetra-ortho-substituted biaryls by NHC-catalyzed Suzuki-Miyaura couplings

AU - Wu, Linglin

AU - Drinkel, Emma

AU - Gaggia, Fiona

AU - Capolicchio, Samanta

AU - Linden, Anthony

AU - Falivene, Laura

AU - Cavallo, Luigi

AU - Dorta, Reto

PY - 2011/11/11

Y1 - 2011/11/11

N2 - Into the groove: The introduction of a C 2-symmetric N-heterocyclic carbene ligand with appropriately substituted naphthyl side chains enables the efficient Suzuki-Miyaura coupling to form bulky tetra-ortho-substituted biaryls from aryl bromides and chlorides at room temperature. DFT calculations uncover the subtle steric phenomena at play that lead to the superior catalytic performance. Cyoct=cyclooctyl.

AB - Into the groove: The introduction of a C 2-symmetric N-heterocyclic carbene ligand with appropriately substituted naphthyl side chains enables the efficient Suzuki-Miyaura coupling to form bulky tetra-ortho-substituted biaryls from aryl bromides and chlorides at room temperature. DFT calculations uncover the subtle steric phenomena at play that lead to the superior catalytic performance. Cyoct=cyclooctyl.

KW - N-heterocyclic carbene ligand

KW - biaryls

KW - cross-coupling

KW - palladium

UR - http://www.scopus.com/inward/record.url?scp=80555144134&partnerID=8YFLogxK

U2 - 10.1002/chem.201102442

DO - 10.1002/chem.201102442

M3 - Article

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AN - SCOPUS:80555144134

SN - 0947-6539

VL - 17

SP - 12886

EP - 12890

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 46

ER -

Room-temperature synthesis of tetra-ortho-substituted biaryls by NHC-catalyzed Suzuki-Miyaura couplings

Abstract

Keywords

ASJC Scopus subject areas

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