Cerium ammonium nitrate-catalyzed aerobic oxidative coupling of dithiocarbamates: facile synthesis of thioureas and bis(aminothiocarbonyl)disulfides

Tian-Tian Li; Xiang-Hai Song; Mei-Shuang Wang; Ning Ma

doi:10.1039/C4RA04628E

Cerium ammonium nitrate-catalyzed aerobic oxidative coupling of dithiocarbamates: facile synthesis of thioureas and bis(aminothiocarbonyl)disulfides

Tian-Tian Li,^a Xiang-Hai Song,^a Mei-Shuang Wang^a and Ning Ma*^a^b

Author affiliations

* Corresponding authors

^a Department of Chemistry, School of Science, Tianjin University, Tianjin 300072, China

^b Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, China
E-mail: mntju@tju.edu.cn
Fax: +86-22-27403475

Abstract

Diverse disubstituted and trisubstituted thioureas were synthesized by the condensation of dithiocarbamate TEA (or DABCO) salts and amines using cerium ammonium nitrate (CAN) as a catalyst in high yields at room temperature. It is a one-pot method and it is unnecessary to isolate isothiocyanates. This reaction probably took place through nucleophilic addition of amines to isothiocyanates, which were generated by oxidative coupling of dithiocarbamates and the following decomposition of bis(aminothiocarbonyl)disulfides. When secondary amines and CS₂ served as the reactants, bis(aminothiocarbonyl)disulfides were obtained via tandem nucleophilic addition/oxidative coupling reactions in moderate to excellent yields. In all the coupling reactions, the oxidant was air and CAN possibly acted as an SET catalyst.

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Publication details

The article was received on 16 May 2014, accepted on 18 Aug 2014 and first published on 18 Aug 2014

Article type: Paper

DOI: 10.1039/C4RA04628E

Citation: RSC Adv., 2014,4, 40054-40060

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Cerium ammonium nitrate-catalyzed aerobic oxidative coupling of dithiocarbamates: facile synthesis of thioureas and bis(aminothiocarbonyl)disulfides

T. Li, X. Song, M. Wang and N. Ma, RSC Adv., 2014, 4, 40054
DOI: 10.1039/C4RA04628E
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Cerium ammonium nitrate-catalyzed aerobic oxidative coupling of dithiocarbamates: facile synthesis of thioureas and bis(aminothiocarbonyl)disulfides

Abstract

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Cerium ammonium nitrate-catalyzed aerobic oxidative coupling of dithiocarbamates: facile synthesis of thioureas and bis(aminothiocarbonyl)disulfides

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