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Issue 39, 2013
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Cationic Rh and Ir complexes containing bidentate imidazolylidene–1,2,3-triazole donor ligands: synthesis and preliminary catalytic studies

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Abstract

A series of new cationic Rh(I), Rh(III) and Ir(III) complexes containing hybrid bidentate N-heterocyclic carbene1,2,3-triazolyl donor of general formulae [Rh(CaT)(COD)]BPh4 (2a–d), [Rh(CaT)(CO)2]BPh4 (3a–d) and [M(CaT)(Cp*)Cl]BPh4 (M = Rh, 4a–d; M = Ir, 5a–c), where CaT = bidentate N-heterocyclic carbenetriazolyl ligands, COD = 1,5-cyclooctadiene and Cp* = 1,2,3,4,5-pentamethylcyclopentadienyl, were synthesised. The imidazolium–1,2,3-triazolyl pre-ligands (1a–c and 1e–i) were readily prepared using the Cu(I) catalysed ‘click reaction’ between phenyl azide or benzyl azides with propargyl functionalised imidazolium salts. The single crystal solid state structures of complexes 2a–d; 3a–b; 4a–d and 5a–b confirm the bidentate coordination of the NHC–1,2,3-triazolyl ligand with the NHC coordinating via the ‘normal’ C2-carbon and the 1,2,3-triazolyl donor coordinating via the N3′ atom to form six membered metallocycles. These complexes are the first examples of Rh and Ir complexes containing the hybrid NHC–1,2,3-triazolyl ligands which exhibit a bidentate coordination mode. A number of these complexes showed limited efficiency as catalysts for the intramolecular hydroamination of 4-pentyn-1-amine to 2-methylpyrroline.

Graphical abstract: Cationic Rh and Ir complexes containing bidentate imidazolylidene–1,2,3-triazole donor ligands: synthesis and preliminary catalytic studies

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Publication details

The article was received on 02 Jun 2013, accepted on 06 Aug 2013 and first published on 20 Aug 2013


Article type: Paper
DOI: 10.1039/C3DT51440D
Dalton Trans., 2013,42, 14298-14308

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    Cationic Rh and Ir complexes containing bidentate imidazolylidene–1,2,3-triazole donor ligands: synthesis and preliminary catalytic studies

    K. Q. Vuong, M. G. Timerbulatova, M. B. Peterson, M. Bhadbhade and B. A. Messerle, Dalton Trans., 2013, 42, 14298
    DOI: 10.1039/C3DT51440D

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