Synthetic Access to Ring-Expanded N-Heterocyclic Carbene (RE-NHC) Copper Complexes and their Performance in Click Chemistry

Jonathan W. Hall; Damien Bouchet; Mary F. Mahon; Michael K. Whittlesey; Catherine S.J. Cazin

doi:10.1021/acs.organomet.1c00039

Synthetic Access to Ring-Expanded N-Heterocyclic Carbene (RE-NHC) Copper Complexes and their Performance in Click Chemistry

Jonathan W. Hall, Damien Bouchet, Mary F. Mahon, Michael K. Whittlesey, Catherine S.J. Cazin

Department of Chemistry

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

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Abstract

The facile syntheses of ring-expanded N-heterocyclic carbene (RE-NHC) copper(I) halide complexes are reported. The method makes use of a weak inorganic base in a green solvent. The reaction times can be greatly reduced by use of this weak-base route under microwave irradiation. The easy access to these complexes permits an evaluation of the catalytic activity and reaction profiling of [Cu(RE-NHC)X] complexes in the Huisgen 1,3-cycloaddition reaction.

Original language	English
Pages (from-to)	1252-1261
Number of pages	10
Journal	Organometallics
Volume	40
Issue number	9
Early online date	27 Apr 2021
DOIs	https://doi.org/10.1021/acs.organomet.1c00039
Publication status	Published - 10 May 2021

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1021/acs.organomet.1c00039

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This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organometallics, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.organomet.1c00039
Accepted author manuscript, 1.06 MB

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title = "Synthetic Access to Ring-Expanded N-Heterocyclic Carbene (RE-NHC) Copper Complexes and their Performance in Click Chemistry",

abstract = "The facile syntheses of ring-expanded N-heterocyclic carbene (RE-NHC) copper(I) halide complexes are reported. The method makes use of a weak inorganic base in a green solvent. The reaction times can be greatly reduced by use of this weak-base route under microwave irradiation. The easy access to these complexes permits an evaluation of the catalytic activity and reaction profiling of [Cu(RE-NHC)X] complexes in the Huisgen 1,3-cycloaddition reaction. ",

author = "Hall, {Jonathan W.} and Damien Bouchet and Mahon, {Mary F.} and Whittlesey, {Michael K.} and Cazin, {Catherine S.J.}",

note = "Funding Information: We acknowledge financial support from the EPSRC Centre for Doctoral Training in Catalysis (EP/L016443/1) for J.W.H. and the Erasmus Programme for D.B. For work performed in Ghent, the UGent BOF and FWO are gratefully acknowledged for support. Publisher Copyright: {\textcopyright} Copyright: Copyright 2021 Elsevier B.V., All rights reserved.",

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AU - Bouchet, Damien

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AU - Whittlesey, Michael K.

AU - Cazin, Catherine S.J.

N1 - Funding Information: We acknowledge financial support from the EPSRC Centre for Doctoral Training in Catalysis (EP/L016443/1) for J.W.H. and the Erasmus Programme for D.B. For work performed in Ghent, the UGent BOF and FWO are gratefully acknowledged for support. Publisher Copyright: © Copyright: Copyright 2021 Elsevier B.V., All rights reserved.

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N2 - The facile syntheses of ring-expanded N-heterocyclic carbene (RE-NHC) copper(I) halide complexes are reported. The method makes use of a weak inorganic base in a green solvent. The reaction times can be greatly reduced by use of this weak-base route under microwave irradiation. The easy access to these complexes permits an evaluation of the catalytic activity and reaction profiling of [Cu(RE-NHC)X] complexes in the Huisgen 1,3-cycloaddition reaction.

AB - The facile syntheses of ring-expanded N-heterocyclic carbene (RE-NHC) copper(I) halide complexes are reported. The method makes use of a weak inorganic base in a green solvent. The reaction times can be greatly reduced by use of this weak-base route under microwave irradiation. The easy access to these complexes permits an evaluation of the catalytic activity and reaction profiling of [Cu(RE-NHC)X] complexes in the Huisgen 1,3-cycloaddition reaction.

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Synthetic Access to Ring-Expanded N-Heterocyclic Carbene (RE-NHC) Copper Complexes and their Performance in Click Chemistry

Abstract

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