Reaction Scope and Mechanistic Insights of Nickel-Catalyzed Migratory Suzuki–Miyaura Cross-Coupling

Guoyin Yin presents insights on the reaction scope and mechanism of a migratory Suzuki–Miyaura cross-coupling.

Metal-catalyzed cross-coupling reactions have revolutionized C–C bond disconnections in synthetic chemistry. In this context, β-hydrogen-containing sp3-carbon electrophiles are generally recognized to be more challenging than their sp2-carbon analogues owing to the possibility of β-hydride elimination taking place as side reaction. During the past several decades, extensive efforts have been devoted to avoiding β-hydride elimination and constructing chemical bonds at the sp3-carbon through metal-catalyzed cross-coupling. Recently, migratory cross-coupling reactions have been emerging as a new research field, as these reactions allow the generation of products through an iterative migratory insertion/β-H elimination process. The net result of this process is the controlled functionalization of a carbon atom different from the one originally carrying the metal.
In 2017, the group of Professor Guoyin Yin (Wuhan University, P. R. of China) began their research in this field and the migratory Suzuki–Miyaura cross-coupling represents the latest progress of the group in this field.

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