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Thiocarbonyl Surrogate via Combination of Sulfur and Chloroform for Thiocarbamide and Oxazolidinethione Construction

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† 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
*E-mail: [email protected]
Cite this: Org. Lett. 2017, 19, 8, 2166–2169
Publication Date (Web):April 7, 2017
https://doi.org/10.1021/acs.orglett.7b00819
Copyright © 2017 American Chemical Society
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    Abstract

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    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.

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