Synfacts 2010(1): 0046-0046  
DOI: 10.1055/s-0029-1218412
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Reversing the Trend in Oxidative Addition

Contributor(s): Timothy M. Swager, Jason R. Cox
O. V. Zenkina, A. Karton, L. J. W. Shimon, J. M. L. Martin*, M. E. van der Boom*
The Weizmann Institute of Science, Rehovot, Israel
Further Information

Publication History

Publication Date:
21 December 2009 (online)

Significance

The oxidative additions of a series of trans-stilbenes with platinum were investigated. It was found that the coordination of the platinum center to the alkene moiety is kinetically preferred over the oxidative addition and that insertion into the Ar-X bond is the rate-determining step. The insertion into the Ar-Br bond was found to be faster than the insertion into the Ar-I bond and electron-withdrawing substituents on the aryl ring slowed down the rate of oxidative addition (k OA), contrary to the general trend in oxidative additions with palladium.