A multicomponent CuAAC “click” approach to a library of hybrid polydentate 2-pyridyl-1,2,3-triazole ligands: new building blocks for the generation of metallosupramolecular architectures

Abstract

A one pot, multicomponent CuAAC reaction has been exploited for the safe generation of alkyl, benzyl or aryl linked polydentate pyridyl-1,2,3-triazole ligands from their corresponding halides, sodium azide and alkynes in excellent yields. The ligands have been fully characterised by elemental analysis, HR-ESMS, IR, (1)H and (13)C NMR and in two cases the structures were confirmed by X-ray crystallography. Additionally, we have examined the Ag(I) coordination chemistry of these ligands and found, using HR-ESMS, (1)H NMR, and X-ray crystallography, that both discrete and polymeric metallosupramolecular architectures can be formed.

RETRACTED ARTICLE: Reduction of carbon dioxide to oxalate by a binuclear copper complex

“…To improve their solubility and hence widen the scope of host-guest chemistry, we replaced the anions with the more hydrophobic PF 6 À ( Fig. 1 27 , as is frequently done to produce Cu(I) catalysts in situ for the well-known 'click' (azide-alkyne cyclization) reaction 28,29 .…”

The btp [2,6-bis(1,2,3-triazol-4-yl)pyridine] binding motif: a new versatile terdentate ligand for supramolecular and coordination chemistry

“…This setback was largely overcome by the development of the CuAAC reaction 66,69 which is a regioselective, high yielding and tolerant reaction, exclusively giving 1,4-disubstituted 1,2,3-triazole products. 70,71 Both the azide and alkyne groups, which form the substrates for the CuAAC reaction, have a wide range of advantages. Both are stable in the presence of nucleophiles, electrophiles, solvents and molecular oxygen, which are common under standard reaction conditions.…”

“…Solvent choice has relatively little effect on yields, and it appears to be a matter of preference and, sometimes, solubility of starting materials that determines the choice of solvent systems. Alcohols like ethanol 87,95,97,98 and tert-butyl alcohol 93,94,96 mixed with water are most common in the literature, while DMSO (with 99 or without 100 water), THF, 60 CH 3 CN 101 and DMF 70,91 are also attested.…”

“…Such behaviour has also been observed for the analogous 2,6-bis-(1,2,3-triazol-4-yl)benzene ligand, btb. 70 …”

Alkali and Alkaline Earth Metal Complexes Ligated by an Ethynyl Substituted Cyclopentadienyl Ligand

“…For this reason, we became aware of the ligand trimethysilylethynyltetramethylcyclopentadiene CpMe 4 (C≡CSiMe 3 )H. CpMe 4 (C≡CSiMe 3 ) − has been used before in group 8 chemistry. The postmodification of η 5 -CpMe 4 (C≡CSiMe 3 ) − metal complexes may include access to metal acetylides [13,14], metal alkyne complexes [15,16], Sonogashira couplings [17][18][19], click reactions [20,21] and cyclizations [22][23][24]. : Na1-C6 2.691(4), Na1-C7 2.673(4), Na1-C8 2.672(4), Na1-C9 2.717(4), Na1-C10 2.736(4), C4-C5 1.223(6), Na1-O1 2.289(3), Na1-O2 2.321(3), Na1-O3 2.293(3), O1-Na1-O2 96.70(2), O2-Na1-O3 95.75 (12), O3-Na1-O1 96.14 (12).…”