17983-74-3Relevant academic research and scientific papers
Fluorinated Anions Promoted "on Water" Activity of Di- and Tetranuclear Copper(I) Catalysts for Functional Triazole Synthesis
Saha, Sayantani,Kaur, Mandeep,Bera, Jitendra K.
, p. 3047 - 3054 (2015)
A set of di- and tetra-copper(I) compounds [Cu2(L1H)2][BArF]2 (1) (L1H = bis(5,7-dimethyl-1,8-naphthyridin-2-yl)amine; BArF = [B{C6H3(CF3)2}4]) and [Cu4(L1)2(L2)2][BNBF]2 (2) (L2 = 5,7-dimethyl-1,8-naphthyridin-2-amine; BNBF = [NH2{B(C6F5)3}2]), stabilized by naphthyridine-based ligands and containing fluorinated anions, is synthesized. Their catalytic utility for copper(I)-catalyzed azide-alkyne coupling (CuAAC) reactions in organic solvents and "on water" is evaluated. The dimer analogue [Cu2(L1H)2][BPh4]2 (3) with nonfluorinated anion is synthesized for the purpose of comparison. All three compounds show CuAAC activity in organic solvents, although the performance of 3 is considerably lower. Remarkable rate enhancement is displayed by compounds containing fluorinated anions (1 and 2) under "on water" conditions for the model reaction involving benzyl azide, affording 98% conversions in 15-20 min, where compound 3 gives 76% conversions in 50 min. Kinetic experiments reveal the involvement of two coppers in the cycloaddition process. Employing a host of substrates, the usefulness of fluorinated anions to dramatically improve the catalytic activity of Cu(I) compounds under "on water" conditions is demonstrated. (Figure Presented).
"Click chemistry" in zeolites: Copper(I) zeolites as new heterogeneous and ligand-free catalysts for the huisgen [3+2] cycloaddition
Chassaing, Stefan,Sido, Abdelkarim Sani Souna,Alix, Aurelien,Kumarraja, Mayilvasagam,Pale, Patrick,Sommer, Jean
supporting information; experimental part, p. 6713 - 6721 (2009/07/11)
For the first time, copper(I)-exchanged zeolites were developed as catalysts in organic synthesis. These solid materials proved to be versatile and efficient heterogeneous, ligand-free catalytic systems for the Huisgen [3+2] cycloaddition. These cheap and
