一种从 1,4-烯二酮和硫醇一锅法合成硫代杂环呋喃的无金属方法。
A one-pot metal-free protocol for the synthesis of chalcogenated furans from 1,4-enediones and thiols.
机构信息
Department of Chemistry, National Institute of Technology, Tiruchirappalli, Tamil Nadu-620015, India.
出版信息
Org Biomol Chem. 2019 Jan 23;17(4):982-991. doi: 10.1039/c8ob03051k.
Transition-metal-free synthesis of chalcogenated furans through the sequential thiol-Michael/Paal-Knorr reaction of 1,4-enediones in the presence of a catalytic amount of p-toluenesulfonic acid has been developed. The present one-pot strategy involves the thiol Michael addition to 1,4-enediones in an anti-Markovnikov fashion with the formation of a new C-S bond, followed by intramolecular dehydrative annulation in the presence of cat. TsOH delivering fully substituted furans in good to excellent yields (50-99%). The reaction is compatible with a wide range of substrates and also capable of multi-gram scale synthesis of chalcogenated furans.
在催化量的对甲苯磺酸存在下，通过 1,4-烯二酮的顺序硫醇迈克尔/Paal-Knorr 反应，实现了无过渡金属合成硫代呋喃。本一锅法策略涉及硫醇迈克尔加成到 1,4-烯二酮中，以反 Markovnikov 方式形成新的 C-S 键，然后在 cat. TsOH 的存在下进行分子内脱水环化，以良好至优异的收率（50-99%）得到完全取代的呋喃。该反应与广泛的底物兼容，也能够进行多克规模的硫代呋喃合成。
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