Neutral dinuclear copper(I)-NHC complexes: synthesis and application in the hydrosilylation of ketones

Michael Trose; Faima Lazreg; Tao Chang; Fady Nahra; David B. Cordes; Alexandra M. Z. Slawin; Catherine S. J. Cazin

doi:10.1021/acscatal.6b02723

Neutral dinuclear copper(I)-NHC complexes: synthesis and application in the hydrosilylation of ketones

Michael Trose, Faima Lazreg, Tao Chang, Fady Nahra, David B. Cordes, Alexandra M. Z. Slawin, Catherine S. J. Cazin^*

^*Corresponding author for this work

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

Abstract

The synthesis of a class of highly stable neutral dinuclear Cu(I)-NHC complexes using 1,2,4-triazole as a bridging ligand is described. Various NHCs were used to generate a library of [Cu(μ-trz)(NHC)]₂, complexes. Interestingly, [Cu(μ-trz)(IPr)]₂ was found to be highly active in the hydrosilylation of ketones, without the need for an external base or any other additive. A wide range of aryl and alkyl ketones, as well as sterically hindered ketones, was successfully reduced to alcohols using the lowest catalyst loading reported to date.

Original language	English
Pages (from-to)	238-242
Number of pages	5
Journal	ACS Catalysis
Volume	7
Issue number	1
Early online date	6 Dec 2016
DOIs	https://doi.org/10.1021/acscatal.6b02723
Publication status	Published - 6 Jan 2017

Keywords

N-heterocyclic carbenes
Copper(I)
Hydrosilylation
Ketones
Dinuclear

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10.1021/acscatal.6b02723

MT_dimer_MS_23092016_ACSCat[1]
Copyright © 2016 American Chemical Society. This work has been 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://doi.org/10.1021/acscatal.6b02723
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Cite this

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title = "Neutral dinuclear copper(I)-NHC complexes: synthesis and application in the hydrosilylation of ketones",

abstract = "The synthesis of a class of highly stable neutral dinuclear Cu(I)-NHC complexes using 1,2,4-triazole as a bridging ligand is described. Various NHCs were used to generate a library of [Cu(μ-trz)(NHC)]2, complexes. Interestingly, [Cu(μ-trz)(IPr)]2 was found to be highly active in the hydrosilylation of ketones, without the need for an external base or any other additive. A wide range of aryl and alkyl ketones, as well as sterically hindered ketones, was successfully reduced to alcohols using the lowest catalyst loading reported to date.",

keywords = "N-heterocyclic carbenes, Copper(I), Hydrosilylation, Ketones, Dinuclear",

author = "Michael Trose and Faima Lazreg and Tao Chang and Fady Nahra and Cordes, {David B.} and Slawin, {Alexandra M. Z.} and Cazin, {Catherine S. J.}",

note = "The authors gratefully acknowledge the Royal Society (University Research Fellowship to C.S.J.C.) for funding.",

year = "2017",

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doi = "10.1021/acscatal.6b02723",

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T1 - Neutral dinuclear copper(I)-NHC complexes

T2 - synthesis and application in the hydrosilylation of ketones

AU - Trose, Michael

AU - Lazreg, Faima

AU - Chang, Tao

AU - Nahra, Fady

AU - Cordes, David B.

AU - Slawin, Alexandra M. Z.

AU - Cazin, Catherine S. J.

N1 - The authors gratefully acknowledge the Royal Society (University Research Fellowship to C.S.J.C.) for funding.

PY - 2017/1/6

Y1 - 2017/1/6

N2 - The synthesis of a class of highly stable neutral dinuclear Cu(I)-NHC complexes using 1,2,4-triazole as a bridging ligand is described. Various NHCs were used to generate a library of [Cu(μ-trz)(NHC)]2, complexes. Interestingly, [Cu(μ-trz)(IPr)]2 was found to be highly active in the hydrosilylation of ketones, without the need for an external base or any other additive. A wide range of aryl and alkyl ketones, as well as sterically hindered ketones, was successfully reduced to alcohols using the lowest catalyst loading reported to date.

AB - The synthesis of a class of highly stable neutral dinuclear Cu(I)-NHC complexes using 1,2,4-triazole as a bridging ligand is described. Various NHCs were used to generate a library of [Cu(μ-trz)(NHC)]2, complexes. Interestingly, [Cu(μ-trz)(IPr)]2 was found to be highly active in the hydrosilylation of ketones, without the need for an external base or any other additive. A wide range of aryl and alkyl ketones, as well as sterically hindered ketones, was successfully reduced to alcohols using the lowest catalyst loading reported to date.

KW - N-heterocyclic carbenes

KW - Copper(I)

KW - Hydrosilylation

KW - Ketones

KW - Dinuclear

UR - http://pubs.acs.org/doi/suppl/10.1021/acscatal.6b02723

U2 - 10.1021/acscatal.6b02723

DO - 10.1021/acscatal.6b02723

M3 - Article

SN - 2155-5435

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EP - 242

JO - ACS Catalysis

JF - ACS Catalysis

IS - 1

ER -

Neutral dinuclear copper(I)-NHC complexes: synthesis and application in the hydrosilylation of ketones

Abstract

Keywords

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