Elsevier

Tetrahedron Letters

Volume 57, Issue 12, 23 March 2016, Pages 1313-1316
Tetrahedron Letters

Evaluation of dipole moment and electrophilicity on the nature of click-type coupling reaction between thioamide and sulfonyl azide

https://doi.org/10.1016/j.tetlet.2016.02.028Get rights and content

Abstract

A cooperated experimental and computational investigation on sulfonyl amidine formation from thioamides and sulfonyl azides is described. The data support a non-concerted two-step pathway for the coupling reaction and also indicate that dipole moment of thioamide and electrophilicity of sulfonyl azide would be significant factors for the reaction efficiency. A simple reactivity prediction of the coupling reaction was demonstrated by preliminary in silico evaluation for these factors, by which we successfully picked up a good pair of reactants with a high reactivity among several thioamides and sulfonyl azides in stock.

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Acknowledgments

This research was supported by Grants-in-Aid for Scientific Research (25350976 (J.C.)) from the Ministry of Education, Culture, Sports, Science and Technology of Japan, and Adaptable and Seamless Technology Transfer Program (A-STEP, AS262Z01488Q (J.C.)) through target-driven R&D, JST. M.A. is a recipient of Directorate General of Higher Education Scholarship from the Ministry of Research, Technology, and Higher Education of the Republic of Indonesia.

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