During the past three decades, the bond formations (C-C, C-X) promoted by transition metals are extensively studied, and widely applied in the organic syntheses as the most successful, and reliable methods. In general, this transformation includes three elementary reactions: (1) oxidative addition, (2) Transmetallation, (3) Reductive Elimination. Herein, we would like to introduce a new approach: the oxidative cross-coupling, which involves double transmetallation,
1-3 and reductive elimination (Scheme 1). Using desyl chloride as the oxidant, a Csp-Sn reagent and a Csp3-Zn reagent can couple together with surprisingly high selectivity.
4 When the Csp3-Zn reagents have b-H, the coupling can take place well in high yield as well as the selectivity. The coupling of Csp-Sn and Csp2-Zn was also examined, and high yield of the desired cross-coupling products were obtained. Our kinetic data from ReactorIR,
13C NMR indicate that the organozinc reagents are highly oxophilic, and the organotin reagent might be halophilic.

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