Saha, Sayantani ; Kaur, Mandeep ; Bera, Jitendra K. (2015) Fluorinated anions promoted "on water" activity of di- and tetranuclear copper(I) catalysts for functional triazole synthesis Organometallics, 34 (12). pp. 3047-3054. ISSN 0276-7333
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Official URL: http://pubs.acs.org/doi/abs/10.1021/acs.organomet....
Related URL: http://dx.doi.org/10.1021/acs.organomet.5b00348
Abstract
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.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 99847 |
| Deposited On: | 27 Nov 2016 13:29 |
| Last Modified: | 27 Nov 2016 13:29 |
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