Use of ring-expanded diamino- and diamidocarbene ligands in copper catalyzed azide-alkyne "click" reactions

Lee R. Collins; Thomas M. Rookes; Mary F. Mahon; Ian M. Riddlestone; Michael K. Whittlesey

doi:10.1021/om5004732

Use of ring-expanded diamino- and diamidocarbene ligands in copper catalyzed azide-alkyne "click" reactions

Lee R. Collins, Thomas M. Rookes, Mary F. Mahon, Ian M. Riddlestone, Michael K. Whittlesey

Department of Chemistry

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

29 Citations (SciVal)

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Abstract

The two-coordinate ring-expanded N-heterocyclic carbene copper(I) complexes [Cu(RE-NHC)₂]⁺ (RE-NHC = 6-Mes, 7-o-Tol, 7-Mes) have been prepared and shown to be effective catalysts under neat conditions for the 1,3-dipolar cycloaddition of alkynes and azides. In contrast, the cationic diamidocarbene analogue [Cu(6-MesDAC)₂]⁺ and the neutral species [(6-MesDAC)CuCl]₂ and [(6-MesDAC)₂(CuCl)₃] show good activity when the catalysis is performed on water.

Original language	English
Pages (from-to)	5882-5887
Number of pages	6
Journal	Organometallics
Volume	33
Issue number	20
Early online date	25 Jun 2014
DOIs	https://doi.org/10.1021/om5004732
Publication status	Published - 27 Oct 2014

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10.1021/om5004732

Whittlesey revised manuscript for OPUS
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 http://pubs.acs.org/doi/abs/10.1021/om5004732
Accepted author manuscript, 1.11 MB

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title = "Use of ring-expanded diamino- and diamidocarbene ligands in copper catalyzed azide-alkyne {"}click{"} reactions",

abstract = "The two-coordinate ring-expanded N-heterocyclic carbene copper(I) complexes [Cu(RE-NHC)2]+ (RE-NHC = 6-Mes, 7-o-Tol, 7-Mes) have been prepared and shown to be effective catalysts under neat conditions for the 1,3-dipolar cycloaddition of alkynes and azides. In contrast, the cationic diamidocarbene analogue [Cu(6-MesDAC)2]+ and the neutral species [(6-MesDAC)CuCl]2 and [(6-MesDAC)2(CuCl)3] show good activity when the catalysis is performed on water.",

author = "Collins, {Lee R.} and Rookes, {Thomas M.} and Mahon, {Mary F.} and Riddlestone, {Ian M.} and Whittlesey, {Michael K.}",

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doi = "10.1021/om5004732",

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T1 - Use of ring-expanded diamino- and diamidocarbene ligands in copper catalyzed azide-alkyne "click" reactions

AU - Collins, Lee R.

AU - Rookes, Thomas M.

AU - Mahon, Mary F.

AU - Riddlestone, Ian M.

AU - Whittlesey, Michael K.

PY - 2014/10/27

Y1 - 2014/10/27

N2 - The two-coordinate ring-expanded N-heterocyclic carbene copper(I) complexes [Cu(RE-NHC)2]+ (RE-NHC = 6-Mes, 7-o-Tol, 7-Mes) have been prepared and shown to be effective catalysts under neat conditions for the 1,3-dipolar cycloaddition of alkynes and azides. In contrast, the cationic diamidocarbene analogue [Cu(6-MesDAC)2]+ and the neutral species [(6-MesDAC)CuCl]2 and [(6-MesDAC)2(CuCl)3] show good activity when the catalysis is performed on water.

AB - The two-coordinate ring-expanded N-heterocyclic carbene copper(I) complexes [Cu(RE-NHC)2]+ (RE-NHC = 6-Mes, 7-o-Tol, 7-Mes) have been prepared and shown to be effective catalysts under neat conditions for the 1,3-dipolar cycloaddition of alkynes and azides. In contrast, the cationic diamidocarbene analogue [Cu(6-MesDAC)2]+ and the neutral species [(6-MesDAC)CuCl]2 and [(6-MesDAC)2(CuCl)3] show good activity when the catalysis is performed on water.

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UR - http://dx.doi.org/10.1021/om5004732

U2 - 10.1021/om5004732

DO - 10.1021/om5004732

M3 - Article

SN - 0276-7333

VL - 33

SP - 5882

EP - 5887

JO - Organometallics

JF - Organometallics

IS - 20

ER -

Use of ring-expanded diamino- and diamidocarbene ligands in copper catalyzed azide-alkyne "click" reactions

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Catalytic Functionalisation of Aromatic Fluorocarbons

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Use of ring-expanded diamino- and diamidocarbene ligands in copper catalyzed azide-alkyne "click" reactions

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Catalytic Functionalisation of Aromatic Fluorocarbons

500 MHZ NMR SPECTROMETER TO SUPPORT ORGANIC, BIO-ORGANIC AND INORGANIC CHEMISTRY

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MC2- Nuclear Magnetic Resonance (NMR)

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