In Quest of “Stereoselective Switch” for On-Water Hydrothiolation of Terminal Alkynes Using Different Additives and Green Synthesis of Vicinal Dithioethers

B. Basu, Kinkar Biswas, S. Kundu, Debasish Sengupta
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引用次数: 3

Abstract

On-water hydrothiolation reaction between terminal alkyne and thiol has been probed in the presence of various additives. Aromatic alkynes yield corresponding 1-alkenyl sulfides, whereas aliphatic alkynes undergo double-addition yielding vicinal disulfides in good to excellent yields. Formation of 1-alkenyl sulfides proceeds with a high degree of regioselectivity (via anti-Markovnikov addition), and switching the stereoselectivity between E/Z isomers has been noticeably realized in the presence of different additives/promoters.
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不同添加剂对末端炔在水中加氢硫基化的“立体选择开关”探索及邻二硫醚的绿色合成
在不同添加剂的作用下,探讨了末端炔与硫醇在水中的氢硫化反应。芳香族炔烃生成相应的1-烯基硫化物,而脂肪族炔烃经过两次加成生成邻二硫化物,收率很高。1-烯基硫化物的形成具有高度的区域选择性(通过反马尔可夫尼科夫加成),并且在不同添加剂/促进剂的存在下,E/Z异构体之间的立体选择性转换已经明显实现。
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