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N,N'-Di-Boc-Substituted Thiourea as a Novel and Mild Thioacylating Agent Applicable for the Synthesis of Thiocarbonyl Compounds

Biao-Lin Yin*, Zhao-Gui Liu, Jian-Cun Zhang, Zheng-Rong Li

*School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640, P. R. of China, Email:

B.-L. Yin, Z.-G. Liu, J.-C. Zhang, Z.-R. Li, Synthesis, 2010, 991-999.

DOI: 10.1055/s-0029-1219273

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Stable and readily available N,N'-di-Boc-substituted thiourea can be used as a mild thioacylating agent when activated with trifluoroacetic acid anhydride. Through thioacylation of nucleophiles, such as amines, alcohols, thiols, sodium benzene­thiolate, and sodium malonates, a series of thiocarbonyl compounds were prepared with good chemical selectivity and functional group tolerance.

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Key Words

N,N'-di-Boc-substituted thiourea, thioacylating agent, thiocarbonyl, thioureas, thiocarbamates

ID: J66-Y2010-0760