Generalization of the copper to late-transition-metal transmetallation to carbenes beyond N-heterocyclic carbenes

Yannick D. Bidal; Orlando Santoro; Mohand Melaimi; David B. Cordes; Alexandra M. Z. Slawin; Guy Bertrand; Catherine S. J. Cazin

doi:10.1002/chem.201601254

Generalization of the copper to late-transition-metal transmetallation to carbenes beyond N-heterocyclic carbenes

Yannick D. Bidal, Orlando Santoro, Mohand Melaimi, David B. Cordes, Alexandra M. Z. Slawin, Guy Bertrand, Catherine S. J. Cazin

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

Abstract

Carbene transition-metal complexes have become a prevalent family of catalysts enabling numerous organic transformations. Their facile synthetic access is a matter of great importance. To this end, the Cu^I-NHC transfer methodology has emerged as a powerful alternative presenting attractive advantages over other methods. Herein, we report the remarkable ability of copper to transfer not only NHCs but also other types of carbenes such as abnormal NHCs (aNHCs), cyclic (alkyl)(amino)carbenes (CAACs), and mesoionic carbenes (MICs) to various transition metal precursors.

Original language	English
Pages (from-to)	9404-9409
Number of pages	6
Journal	Chemistry - A European Journal
Volume	22
Issue number	27
Early online date	30 May 2016
DOIs	https://doi.org/10.1002/chem.201601254
Publication status	Published - 23 Jun 2016

Keywords

Abnormal
CAAC
Carbene transfer
Copper
N-heterocyclic carbene

Access to Document

10.1002/chem.201601254

Cazin_2016_CEJ_Copper_AM
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://dx.doi.org/10.1002/chem.201601254
Accepted author manuscript, 619 KB

Cite this

@article{522ad7d257c0473bb4b771a90959cd4b,

title = "Generalization of the copper to late-transition-metal transmetallation to carbenes beyond N-heterocyclic carbenes",

abstract = "Carbene transition-metal complexes have become a prevalent family of catalysts enabling numerous organic transformations. Their facile synthetic access is a matter of great importance. To this end, the CuI-NHC transfer methodology has emerged as a powerful alternative presenting attractive advantages over other methods. Herein, we report the remarkable ability of copper to transfer not only NHCs but also other types of carbenes such as abnormal NHCs (aNHCs), cyclic (alkyl)(amino)carbenes (CAACs), and mesoionic carbenes (MICs) to various transition metal precursors.",

keywords = "Abnormal, CAAC, Carbene transfer, Copper, N-heterocyclic carbene",

author = "Bidal, \{Yannick D.\} and Orlando Santoro and Mohand Melaimi and Cordes, \{David B.\} and Slawin, \{Alexandra M. Z.\} and Guy Bertrand and Cazin, \{Catherine S. J.\}",

note = "The authors gratefully acknowledge the Royal Society (University Research Fellowship to C.S.J.C.), the EPSRC (EP/J500549/1) and the DOE (DE-FG02-13ER16370) for financial support.",

year = "2016",

month = jun,

day = "23",

doi = "10.1002/chem.201601254",

language = "English",

volume = "22",

pages = "9404--9409",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "John Wiley \& Sons, Ltd",

number = "27",

}

TY - JOUR

T1 - Generalization of the copper to late-transition-metal transmetallation to carbenes beyond N-heterocyclic carbenes

AU - Bidal, Yannick D.

AU - Santoro, Orlando

AU - Melaimi, Mohand

AU - Cordes, David B.

AU - Slawin, Alexandra M. Z.

AU - Bertrand, Guy

AU - Cazin, Catherine S. J.

N1 - The authors gratefully acknowledge the Royal Society (University Research Fellowship to C.S.J.C.), the EPSRC (EP/J500549/1) and the DOE (DE-FG02-13ER16370) for financial support.

PY - 2016/6/23

Y1 - 2016/6/23

N2 - Carbene transition-metal complexes have become a prevalent family of catalysts enabling numerous organic transformations. Their facile synthetic access is a matter of great importance. To this end, the CuI-NHC transfer methodology has emerged as a powerful alternative presenting attractive advantages over other methods. Herein, we report the remarkable ability of copper to transfer not only NHCs but also other types of carbenes such as abnormal NHCs (aNHCs), cyclic (alkyl)(amino)carbenes (CAACs), and mesoionic carbenes (MICs) to various transition metal precursors.

AB - Carbene transition-metal complexes have become a prevalent family of catalysts enabling numerous organic transformations. Their facile synthetic access is a matter of great importance. To this end, the CuI-NHC transfer methodology has emerged as a powerful alternative presenting attractive advantages over other methods. Herein, we report the remarkable ability of copper to transfer not only NHCs but also other types of carbenes such as abnormal NHCs (aNHCs), cyclic (alkyl)(amino)carbenes (CAACs), and mesoionic carbenes (MICs) to various transition metal precursors.

KW - Abnormal

KW - CAAC

KW - Carbene transfer

KW - Copper

KW - N-heterocyclic carbene

UR - https://www.scopus.com/pages/publications/84971401706

U2 - 10.1002/chem.201601254

DO - 10.1002/chem.201601254

M3 - Article

SN - 0947-6539

VL - 22

SP - 9404

EP - 9409

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 27

ER -

Generalization of the copper to late-transition-metal transmetallation to carbenes beyond N-heterocyclic carbenes

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Catalytic C-H bond functionalisation: Catalytic C-H bond functionalisation

Alexandra Slawin