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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
+ Author Affiliations
- Author Affiliations

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:,

James obtained his B.Sc. (Hons) (1998) and M.Sc. (2000) from Victoria University of Wellington and completed his PhD (2000–2005) at the University of Chicago under the direction of Prof. Brice Bosnich. In 2005 he moved to Prof. David Leigh's group at the University of Edinburgh, where he was awarded a British Ramsay Memorial Trust Fellowship (2006–2008), to carry out research on molecular machines. He started his independent career at the University of Otago in 2008 and was promoted to Senior Lecturer in 2011. His major research interests are in catalysis, self-assembly, molecular recognition and the development of molecular machines.

Ai-Lan hails from Malaysia and obtained her MSci(Hons) (2000) and Ph.D. (2004) from the University of Cambridge, working under the supervision of Prof. Steven V. Ley. She was subsequently awarded a Lindemann Trust Fellowship (2004–2005) to work at Boston College with Prof. Amir H. Hoveyda and Prof. Richard R. Schrock. In 2006, Ai-Lan was appointed as a fixed-term Lecturer at the University of Edinburgh, carrying out research with Prof. David A. Leigh. She has been in her present position as Lecturer at Heriot-Watt University since 2007 and her research interests include gold- and palladium-catalyzed reactions as well as the synthesis of mechanically interlocked architectures.

Kelly obtained her M.Sc. (2005) and Ph.D. (2009) degrees at the University of Waikato, under the supervision of Prof. Bill Henderson and Prof. Brian Nicholson in the field of organometallic gold chemistry. She then moved to the University of Otago to work as a postdoctoral fellow in the Crowley group (2009–2010) on 1,2,3-triazole chemistry. Kelly is currently funded by the New Zealand Science and Technology Postdoctoral Fellowship scheme to work on ruthenium anti-cancer drugs with Prof. Paul Dyson at the Ecole Polytechnique Fédérale de Lausanne (Switzerland).

Australian Journal of Chemistry 64(8) 1118-1132
Submitted: 6 May 2011  Accepted: 4 June 2011   Published: 19 August 2011

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Triply cyclometalated trinuclear iridium(iii) and trinuclear palladium(ii) complexes with a tri-mesoionic carbene ligand
Maity Ramananda, Mekic Amel, van der Meer Margarethe, Verma Amit, Sarkar Biprajit
Chem. Commun.. 2015 51(82). p.15106
Ruthenium(ii) and osmium(ii) 1,2,3-triazolylidene organometallics: a preliminary investigation into the biological activity of ‘click’ carbene complexes
Kilpin Kelly J., Crot Stéphanie, Riedel Tina, Kitchen Jonathan A., Dyson Paul J.
Dalton Trans.. 2014 43(3). p.1443
A mesoionic bis(Py-tzNHC) palladium(ii) complex catalyses “green” Sonogashira reaction through an unprecedented mechanism
Gazvoda Martin, Virant Miha, Pevec Andrej, Urankar Damijana, Bolje Aljoša, Kočevar Marijan, Košmrlj Janez
Chem. Commun.. 2016 52(8). p.1571
Expanding the Scope of Chelating Triazolylidenes: Mesoionic Carbenes from the 1,5-“Click”-Regioisomer and Catalytic Synthesis of Secondary Amines from Nitroarenes
Suntrup Lisa, Hohloch Stephan, Sarkar Biprajit
Chemistry - A European Journal. 2016 22(50). p.18009
Versatile O- and S-functionalized 1,2,3-triazoliums: ionic liquids for the Baylis–Hillman reaction and ligand precursors for stable MIC-transition metal complexes
Mendoza-Espinosa Daniel, González-Olvera Rodrigo, Osornio Cecilia, Negrón-Silva Guillermo E., Santillan Rosa
New J. Chem.. 2015 39(3). p.1587
Activating Azides and Alkynes for the Click Reaction with [Cu(aNHC)2I] or [Cu(aNHC)2]+(aNHC = Triazole-Derived Abnormal Carbenes): Structural Characterization and Catalytic Properties
Hohloch Stephan, Scheiffele Damaris, Sarkar Biprajit
European Journal of Inorganic Chemistry. 2013 2013(22-23). p.3956
Triazolium cations: from the “click” pool to multipurpose applications
Aizpurua Jesus M., Fratila Raluca M., Monasterio Zaira, Pérez-Esnaola Nerea, Andreieff Elena, Irastorza Aitziber, Sagartzazu-Aizpurua Maialen
New J. Chem.. 2014 38(2). p.474
Ein robuster mesoionischer Pyridylcarben-Cobalt-Komplex als Elektrokatalysator für die Wasserstoff-Produktion
van der Meer Margarethe, Glais Estelle, Siewert Inke, Sarkar Biprajit
Angewandte Chemie. 2015 127(46). p.13997
Redox-active multinuclear Pd(ii) complexes with bis- and tris-mesoionic carbenes
Maity Ramananda, van der Meer Margarethe, Sarkar Biprajit
Dalton Trans.. 2015 44(1). p.46
A Mesoionic Carbene as Neutral Ligand for Phosphorescent Cationic Ir(III) Complexes
Baschieri Andrea, Monti Filippo, Matteucci Elia, Mazzanti Andrea, Barbieri Andrea, Armaroli Nicola, Sambri Letizia
Inorganic Chemistry. 2016 55(16). p.7912
Arene–Ruthenium(II) and −Iridium(III) Complexes with “Click”-Based Pyridyl-triazoles, Bis-triazoles, and Chelating Abnormal Carbenes: Applications in Catalytic Transfer Hydrogenation of Nitrobenzene
Hohloch Stephan, Suntrup Lisa, Sarkar Biprajit
Organometallics. 2013 32(24). p.7376

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