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

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.