通过硫和氯仿组合构建硫羰基取代物用于硫代脲和恶唑烷硫酮的合成。
Thiocarbonyl Surrogate via Combination of Sulfur and Chloroform for Thiocarbamide and Oxazolidinethione Construction.
机构信息
Shanghai Key Laboratory of Green Chemistry and Chemical Process, School of Chemistry and Molecular Engineering, East China Normal University , 3663 North Zhongshan Road, Shanghai, 200062, P. R. China.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, P. R. China.
出版信息
Org Lett. 2017 Apr 21;19(8):2166-2169. doi: 10.1021/acs.orglett.7b00819. Epub 2017 Apr 7.
An efficient and practical thiocarbonyl surrogate via combination of sulfur and chloroform has been developed. A variety of thiocarbamides and oxazolidinethiones have been established, including chiral thiourea catalysts and chiral oxazolidinethione auxiliaries with high selectivity. Meanwhile, pesticides Diafenthiuron (an acaricide), ANTU (a rodenticide), and Chloromethiuron (an insecticide) were practically synthesized through this method in gram scale. Dicholorocarbene, as the key intermediate, was further confirmed via a carbene-trapping control experiment.
开发了一种通过硫和氯仿结合的高效实用的硫羰基替代物。已经建立了各种硫代氨基甲酸盐和恶唑烷硫酮，包括具有高选择性的手性硫脲催化剂和手性恶唑烷硫酮助剂。同时，通过该方法在克级规模下实际合成了杀虫剂敌螨通（杀螨剂）、安妥（灭鼠剂）和氯甲噻隆（杀虫剂）。二氯卡宾作为关键中间体，通过卡宾捕获对照实验进一步得到证实。
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