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

Ghent University

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

14 Citations (SciVal)

174 Downloads (Pure)

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

Bibliographical 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:
©

Copyright:
Copyright 2021 Elsevier B.V., All rights reserved.

Funding

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.

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

Access to Document

10.1021/acs.organomet.1c00039

MS_Revised.PDF
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

Cite this

@article{a4419acd4f614da0843dce4bf58bad0f,

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.",

year = "2021",

month = may,

day = "10",

doi = "10.1021/acs.organomet.1c00039",

language = "English",

volume = "40",

pages = "1252--1261",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society",

number = "9",

}

TY - JOUR

T1 - Synthetic Access to Ring-Expanded N-Heterocyclic Carbene (RE-NHC) Copper Complexes and their Performance in Click Chemistry

AU - Hall, Jonathan W.

AU - Bouchet, Damien

AU - Mahon, Mary F.

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.

PY - 2021/5/10

Y1 - 2021/5/10

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.

UR - https://www.scopus.com/pages/publications/85106463418

U2 - 10.1021/acs.organomet.1c00039

DO - 10.1021/acs.organomet.1c00039

M3 - Article

AN - SCOPUS:85106463418

SN - 0276-7333

VL - 40

SP - 1252

EP - 1261

JO - Organometallics

JF - Organometallics

IS - 9

ER -

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

Abstract

Bibliographical note

Funding

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Avance 300 MHz Nuclear Magnetic Resonance (NMR) Spectrometer (1South)

Propulse 500 MHz Nuclear Magnetic Resonance (NMR) Spectrometer (1South)

Cite this

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

Abstract

Bibliographical note

Funding

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Equipment

Avance 300 MHz Nuclear Magnetic Resonance (NMR) Spectrometer (1South)

Propulse 500 MHz Nuclear Magnetic Resonance (NMR) Spectrometer (1South)

Cite this