Synlett 2006(18): 3057-3060  
DOI: 10.1055/s-2006-951501
© Georg Thieme Verlag Stuttgart · New York

A Sterically Bulky Cyclic Thiourea as an Efficient Ligand for Palladium-Catalyzed Aerobic Oxidation of Alcohols

Min Yanga, Kai-Tai Yipa, Jie-Hui Pana, Ying-Chun Chenb, Nian-Yong Zhua, Dan Yang*a
a Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, P. R. of China
Fax: +85228592159; e-Mail:;
b Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, P. R. of China
Further Information

Publication History

Received 17 April 2006
Publication Date:
25 October 2006 (online)


Sterically bulky N,N¢-disubstituted cyclic thiourea ligand L1 has been demonstrated as an efficient ligand in palladium-catalyzed oxidation of alcohols using molecular oxygen as an oxidant. This new catalyst system has been applied to a wide variety of substrates such as benzylic alcohols, aliphatic secondary alcohols and allylic alcohols, producing the corresponding carbonyl compounds in good to excellent yields.

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L1 is a highly efficient ligand for Heck reactions; see ref. 11a. L2-4 were prepared following the similar procedures.


Other reaction parameters, including palladium sources, solvents, and bases, were examined and the reported conditions were found optimal. The effect of 3 Å molecular sieves was found to give deleterious effect on yields because of serious Pd-black formation.