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

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• 作者：Muhammad Aswad^a ; ^b ; Junya Chiba^a ; ^{chiba@pha.u-toyama.ac.jp" class="auth_mail" title="E-mail the corresponding author} ; Takenori Tomohiro^a ; Yasumaru Hatanaka^a
• 关键词：Thioamide ; Dipole moment ; Sulfonyl azide ; Electrophilicity ; Coupling reaction
• 刊名：Tetrahedron Letters
• 出版年：2016
• 出版时间：23 March 2016
• 年：2016
• 卷：57
• 期：12
• 页码：1313-1316
• 全文大小：568 K

文摘

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.