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Synthesis 2010(6): 991-999  
DOI: 10.1055/s-0029-1219273
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Biao-Lin Yin*a, Zhao-Gui Liub, Jian-Cun Zhangb, Zheng-Rong Lia
a School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640, P. R. of China
e-Mail: blyin@scut.edu.cn;
b Guangzhou Institute of Biomedicine & Health, The Chinese Academy of Sciences, Guangzhou International Business Incubator A-3, Guangzhou Science Park, Guangzhou, 510663, P. R. of China
Further Information

Publication History

Received 26 October 2009
Publication Date:
25 January 2010 (online)

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Abstract

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

Key words

N,N′-di-Boc-substituted thiourea - thioacylating agent - thiocarbonyl

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