Shen Shou-Jie, Wang Le-Mei, Gong Guo-Mei, Wang Yan-Jiao, Liang Jin-Yan, Wang Jun-Wen
Key Laboratory of Magnetic Molecules, Magnetic Information Materials Ministry of Education, The School of Chemical and Material Science, Shanxi Normal University Linfen 041004 China
College of Life Science, Shanxi Normal University Linfen 041004 China.
RSC Adv. 2022 Apr 26;12(20):12663-12671. doi: 10.1039/d2ra01117d. eCollection 2022 Apr 22.
An -addition reaction between imides and propargyl sulfonium salts was developed to afford sulfur-containing -vinylimides with moderate to excellent yields. Under the activation of NaOAc·3HO, imides could undergo deprotonation and propargyl sulfonium salts could isomerize to allenic sulfonium salts. The -nucleophilic attack initiates the reaction and gives the desired products. Various imides, including arylimides, aliphatic imides and -(arylsulfonyl) alkyl acylamides, and even bioactive saccharin, thalidomide and pomalidomide could provide organosulfur -vinylimides compounds. The simple, mild and metal-free reaction conditions, the broad scope of substrates, gram-scale synthesis and convenient transformation embody the synthetic superiority of this process.
开发了一种酰亚胺与炔丙基锍盐之间的加成反应，以中等至优异的产率得到含硫的β-乙烯基酰亚胺。在醋酸钠·3H₂O的活化下，酰亚胺可发生去质子化，炔丙基锍盐可异构化为烯丙基锍盐。β-亲核进攻引发反应并得到所需产物。各种酰亚胺，包括芳基酰亚胺、脂肪族酰亚胺和β-（芳基磺酰基）烷基酰胺，甚至生物活性的糖精、沙利度胺和泊马度胺都能提供有机硫β-乙烯基酰亚胺化合物。简单、温和且无金属的反应条件、广泛的底物范围、克级规模的合成以及便捷的转化体现了该方法的合成优势。
