Palladium-Catalyzed R(sp3)-Zn/R(sp)-SnBu3 Oxidative Cross-Coupling

Liqun Jin; Yingsheng Zhao; Haibo Wang; Aiwen Lei

doi:10.1055/s-2007-990863

PSP

Palladium-Catalyzed R(sp³)-Zn/R(sp)-SnBu₃ Oxidative Cross-Coupling

Liqun Jin, Yingsheng Zhao, Haibo Wang, Aiwen Lei*
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, P. R. of China
Fax: +86(27)68754067; e-Mail: aiwenlei@whu.edu.cn;

Abstract

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Abstract

A novel bond formation through oxidative cross-coupling with desyl chloride as the oxidant has been investigated. The coupling can be carried out under mild conditions. The Csp³-center carbon was involved even in the presence of a β-H, and up to 90% of the desired cross-coupling product was obtained with the secondary Csp³-center substrate.

Key words

oxidative cross-coupling - transmetalation - organotin reagents - organozinc reagents - palladium

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References

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The desired cross-coupling product was mixed with 1,2-diphenylethanone, which was formed from the Zn-enolate IV. Efforts to completely separate the two compounds were unsuccessful.