The majority of the C-C bonds are made by the union of a nucleophilic carbon with an electrophilic one. Because nucleophilic carbon reagents are difficult to work with, the metal catalyzed coupling of two electrophiles is an appealing, yet under explored, alternative. As we reported in 2010 and 2012 (JACS. 2010 , 132, 920, JACS. 2012 , 134, 6146), the nickel-catalyzed cross coupling of haloarenes with haloalkanes under reducing conditions is a general and highly cross-selective process. However, because the mechanism and the origin of the cross-selectivity were unclear, further improvement proved challenging. A combination of catalytic, stoichiometric, kinetic, and radical clock studies has revealed for the first time the mechanistic basis for selectivity in cross-electrophile coupling reactions.

Mechanism of the nickel-catalyzed cross coupling of haloalkanes with haloarenes

245th National Meeting (2013)

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