1,3,4-Trisubtituted-1,2,3-Triazol-5-ylidene 'Click' Carbene Ligands: Synthesis, Catalysis and Self-Assembly

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doi:10.1071/CH11185

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Affiliated with RACI

Royal Australian
Chemical Institute

1,3,4-Trisubstituted-1,2,3-Triazol-5-ylidene ‘Click’ Carbene Ligands: Synthesis, Catalysis and Self-Assembly

James D. Crowley ^A ^D, Ai-Lan Lee ^B ^D and Kelly J. Kilpin ^A ^C

^A Department of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand.
^B School of Engineering and Physical Sciences, Chemistry – William H. Perkin Building, Heriot-Watt University, Edinburgh EH14 4AS, UK.
^C Current address: Institut des Sciences et Ingénierie Chimique, Ecole Polytechnique Fédérale de Lausanne (EPFL), CH-1015 Lausanne, Switzerland.
^D Corresponding authors. Email: jcrowley@chemistry.otago.ac.nz, A.Lee@hw.ac.uk

Australian Journal of Chemistry 64(8) 1118-1132 http://dx.doi.org/10.1071/CH11185
Submitted: 6 May 2011 Accepted: 4 June 2011 Published: 19 August 2011





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Abstract

This review examines the use of the Cu(I)-catalyzed 1,3-cycloaddition of organic azides with terminal alkynes (the CuAAC ‘click’ reaction) for development of a novel family of abnormal/mesoionic N-heterocyclic carbenes and their corresponding metal complexes. These 1,3,4-trisubstituted-1,2,3-triazol-5-ylidenes have donor properties that are intermediate between the traditional Arduengo-type imidazol-2-ylidenes and more highly σ-donating abnormal carbenes, such as imidazol-4-ylidenes or pyrazolin-4-ylidenes. Metal complexes of the 1,3,4-trisubstituted-1,2,3-triazol-5-ylidenes have been used as catalysts for a variety of reactions including the CuAAC cycloaddition, Pd cross-couplings, and ring closing/ring opening metathesis. Additionally, ‘click’ carbene ligands have been used to generate self-assembled metallo-macrocycles and novel photosensitizers. The mild, modular CuAAC approach to these ligands should allow the rapid generation of libraries of 1,3,4-trisubstituted-1,2,3-triazol-5-ylidenes that can be further exploited to generate novel catalysts, metallo-pharmaceuticals and materials.

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