Literature DB >> 20449208

New 1,2,3-triazole ligands through click reactions and their palladium and platinum complexes.

David Schweinfurth1, Roberto Pattacini, Sabine Strobel, Biprajit Sarkar.   

Abstract

The new ligands, 1-(4-isopropyl phenyl)-4-(2-pyridyl)-1,2,3-triazole, 1 and 1-(mesityl)-4-(2-pyridyl)-1,2,3-triazole, 2 were prepared by the reactions of the respective azides with 2-ethynylpyridine following the "click method". These ligands together with the reported ligands 1-(phenyl)-4-(2-pyridyl)-1,2,3-triazole, 3 and 1-(benzyl)-4-(2-pyridyl)-1,2,3-triazole, 4 were reacted with palladium and platinum precursors to give mononuclear cis-dichloropalladium and platinum complexes containing the triazole ligands. Structural characterisation of the free ligand 3 shows that the central N-N bond in the triazole ring has double bond character and hence is best described as an "azo-like" N-N double bond. The pyridine ring in 3 has an almost "anti" conformation with respect to the central triazole ring. The metal centers bind to the ligands through the pyridine N and a triazole N atom. The metal-N(triazole) distances are shorter than the metal-N(pyridine) distances. Cyclic voltammograms of the ligands show reduction processes that appear at extreme negative potentials. Coordination of metal centers induces huge anodic shifts of the reduction potentials due to sigma-polarisation by the metal centers. UV/Vis spectra of the ligands and complexes are also discussed. The properties of such chelating triazole ligands towards palladium and platinum centers is being compared and contrasted to the widely used 2,2'-bipyridine ligand.

Entities:  

Year:  2009        PMID: 20449208     DOI: 10.1039/b910660j

Source DB:  PubMed          Journal:  Dalton Trans        ISSN: 1477-9226            Impact factor:   4.390


  6 in total

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2.  Phosphino-Triazole Ligands for Palladium-Catalyzed Cross-Coupling.

Authors:  Yiming Zhao; Huy van Nguyen; Louise Male; Philip Craven; Benjamin R Buckley; John S Fossey
Journal:  Organometallics       Date:  2018-10-17       Impact factor: 3.876

3.  Novel Re(I) tricarbonyl coordination compounds based on 2-pyridyl-1,2,3-triazole derivatives bearing a 4-amino-substituted benzenesulfonamide arm: synthesis, crystal structure, computational studies and inhibitory activity against carbonic anhydrase I, II, and IX isoforms†.

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Review 4.  Computational investigations of click-derived 1,2,3-triazoles as keystone ligands for complexation with transition metals: a review.

Authors:  Tayebeh Hosseinnejad; Fatemeh Ebrahimpour-Malmir; Bahareh Fattahi
Journal:  RSC Adv       Date:  2018-03-29       Impact factor: 4.036

5.  A photoresponsive palladium complex of an azopyridyl-triazole ligand: light-controlled solubility drives catalytic activity in the Suzuki coupling reaction.

Authors:  Attila Kunfi; István Jablonkai; Tamás Gazdag; Péter J Mayer; Péter Pál Kalapos; Krisztina Németh; Tamás Holczbauer; Gábor London
Journal:  RSC Adv       Date:  2021-07-09       Impact factor: 4.036

6.  High yielding synthesis of 2,2'-bipyridine macrocycles, versatile intermediates in the synthesis of rotaxanes.

Authors:  J E M Lewis; R J Bordoli; M Denis; C J Fletcher; M Galli; E A Neal; E M Rochette; S M Goldup
Journal:  Chem Sci       Date:  2016-01-27       Impact factor: 9.825

  6 in total

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