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

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.

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

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45

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.