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Cu(I)/Fe(III) promoted dicarbonylation of aminopyrazole via oxidative CH coupling with methyl ketones

Author:
Rastogi, Gaurav K., Saikia, B-Shriya, Pahari, Pallab, Deb, Mohit L., Baruah, Pranjal K.
Source:
Tetrahedron letters 2019 v.60 no.17 pp. 1189-1192
ISSN:
0040-4039
Subject:
catalysts, chemical reactions, copper, dimethyl sulfoxide, ferric chloride, ketones, moieties, oxygen
Abstract:
Cu(I)/Fe(III) promoted C4-dicarbonylation of 5-aminopyrazole is developed. The strategy involved radical triggered direct oxidative coupling of 5-aminopyrazoles with methyl ketones using aerial oxygen as a source of oxygen in newly generated carbonyl group. CuI is used as catalyst and FeCl3·6H2O is used as additive and the reaction proceeded at 120 °C in DMSO for 9–12 h. It is found that use of Cu(II) catalyst gives the thiomethylated product by reacting with DMSO instead of oxidative coupling. A plausible mechanism is also given.
Agid:
6350571