Synthesis 2008(9): 1415-1419  
DOI: 10.1055/s-2008-1067018
PAPER
© Georg Thieme Verlag Stuttgart · New York

Application of Cyclic Thiourea as an Efficient Ligand in Palladium-Catalyzed Hiyama Cross-Coupling Reactions

Zhi-sheng Wua,b, Min Yang*a, Hong-ling Lia,b, Yan-xing Qi*a
a National Engineering Research Center for Fine Petrochemical Intermediates, Lanzhou Institute of Chemical Physics, Lanzhou 730000, P. R. of China
Fax: +86(931)4968190; e-Mail: minyang1@gmail.com; e-Mail: qiyanxing@gmail.com;
b Graduate School of the Chinese Academy of Sciences, Chinese Academy of Sciences, Beijing 100039, P. R. of China
Further Information

Publication History

Received 25 October 2007
Publication Date:
16 April 2008 (online)

Abstract

Cyclic thiourea has been first utilized as an efficient ligand in palladium-catalyzed Hiyama cross-coupling reactions. In the presence of palladium(II) acetate, N,N′-bis(2,5-di-tert-butylphenyl)-N,N′-ethylenethiourea, tetrabutylammonium fluoride, and dioxane, aryl halides (X = I, Br, Cl) underwent smooth cross coupling with trimethoxy(phenyl)silane to afford the corresponding biaryl products in moderate to excellent yields. Furthermore, the thiourea can be recovered by column chromatography and reused with negligible loss in catalytic activity.

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