N-Heterocyclic carbene copper(I) catalysed N-methylation of amines using CO2

Orlando Santoro; Faima Lazreg; Yury Minenkov; Luigi  Cavallo; Catherine S.J. Cazin

doi:10.1039/C5DT03506F

N-Heterocyclic carbene copper(I) catalysed N-methylation of amines using CO₂

Orlando Santoro, Faima Lazreg, Yury Minenkov, Luigi Cavallo, Catherine S.J. Cazin

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

Abstract

The N-methylation of amines using CO₂ and PhSiH₃ as source of CH₃ was efficiently performed using a N-heterocyclic carbene copper(I) complex. The methodology was found compatible with aromatic and aliphatic primary and secondary amines. Synthetic and computational studies have been carried out to support the proposed reaction mechanism for this transformation.

Original language	English
Pages (from-to)	18138-18144
Journal	Dalton Transactions
Volume	44
Issue number	41
Early online date	30 Sept 2015
DOIs	https://doi.org/10.1039/C5DT03506F
Publication status	Published - 7 Nov 2015

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10.1039/C5DT03506FLicence: CC BY

Santoro_2015_DT_N-Heterocyclic_CC
Copyright 2015 the Authors. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (http://creativecommons.org/licenses/by/3.0/).
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title = "N-Heterocyclic carbene copper(I) catalysed N-methylation of amines using CO2",

abstract = "The N-methylation of amines using CO2 and PhSiH3 as source of CH3 was efficiently performed using a N-heterocyclic carbene copper(I) complex. The methodology was found compatible with aromatic and aliphatic primary and secondary amines. Synthetic and computational studies have been carried out to support the proposed reaction mechanism for this transformation.",

author = "Orlando Santoro and Faima Lazreg and Yury Minenkov and Luigi Cavallo and Cazin, \{Catherine S.J.\}",

note = "The authors gratefully acknowledge the Royal Society (University Research Fellowship to C.S.J.C.), the EPSRC (DTG011 EP/J500549/1) and the King Abdullah University of Science and Technology for funding, and the EPSRC National Mass Spectrometry Service Centre at Swansea University for HMRS analyses. ",

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AU - Santoro, Orlando

AU - Lazreg, Faima

AU - Minenkov, Yury

AU - Cavallo, Luigi

AU - Cazin, Catherine S.J.

N1 - The authors gratefully acknowledge the Royal Society (University Research Fellowship to C.S.J.C.), the EPSRC (DTG011 EP/J500549/1) and the King Abdullah University of Science and Technology for funding, and the EPSRC National Mass Spectrometry Service Centre at Swansea University for HMRS analyses.

PY - 2015/11/7

Y1 - 2015/11/7

N2 - The N-methylation of amines using CO2 and PhSiH3 as source of CH3 was efficiently performed using a N-heterocyclic carbene copper(I) complex. The methodology was found compatible with aromatic and aliphatic primary and secondary amines. Synthetic and computational studies have been carried out to support the proposed reaction mechanism for this transformation.

AB - The N-methylation of amines using CO2 and PhSiH3 as source of CH3 was efficiently performed using a N-heterocyclic carbene copper(I) complex. The methodology was found compatible with aromatic and aliphatic primary and secondary amines. Synthetic and computational studies have been carried out to support the proposed reaction mechanism for this transformation.

UR - http://www.rsc.org/suppdata/c5/dt/c5dt03506f/c5dt03506f1.pdf

UR - https://www.scopus.com/pages/publications/84944214411

U2 - 10.1039/C5DT03506F

DO - 10.1039/C5DT03506F

M3 - Article

SN - 1477-9226

VL - 44

SP - 18138

EP - 18144

JO - Dalton Transactions

JF - Dalton Transactions

IS - 41

ER -

N-Heterocyclic carbene copper(I) catalysed N-methylation of amines using CO₂

Abstract

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

Copper(I)-N-heterocyclic carbene (NHC) complexes: synthesis, characterisation and applications in synthesis and catalysis

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N-Heterocyclic carbene copper(I) catalysed N-methylation of amines using CO2

Abstract

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

Student theses

Copper(I)-N-heterocyclic carbene (NHC) complexes: synthesis, characterisation and applications in synthesis and catalysis

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N-Heterocyclic carbene copper(I) catalysed N-methylation of amines using CO₂