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Issue 38, 2013
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Novel atom-economic reaction: comprehensive utilization of S-alkylisothiouronium salt in the synthesis of thioethers and guanidinium salts

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Abstract

A novel atom-economic three-component one-pot reaction of a primary amine, an S-alkylisothiouronium salt and a Michael receptor is reported, which affords a guanidinium salt and thioether simultaneously. The guanidine moiety is involved in catalyzing the conjugated Michael addition of the mercaptan. The reaction proceeds under ambient conditions using a non-toxic EtOH–H2O mixture as the solvent, and the two products can be very easily purified. Complete atom economy is achieved by fully utilizing the S-alkylisothiouronium salt and converting the previously wasted mercaptan by-product into the valuable thioether.

Graphical abstract: Novel atom-economic reaction: comprehensive utilization of S-alkylisothiouronium salt in the synthesis of thioethers and guanidinium salts

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Publication details

The article was received on 21 May 2013, accepted on 15 Jul 2013, published on 17 Jul 2013 and first published online on 17 Jul 2013


Article type: Paper
DOI: 10.1039/C3RA42503G
Citation: RSC Adv., 2013,3, 17150-17155
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    Novel atom-economic reaction: comprehensive utilization of S-alkylisothiouronium salt in the synthesis of thioethers and guanidinium salts

    P. Gao, P. Leng, Q. Sun, X. Wang, Z. Ge and R. Li, RSC Adv., 2013, 3, 17150
    DOI: 10.1039/C3RA42503G

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