Directed Nickel-Catalyzed Oxidative Heck Coupling Enables by a Tailored H2 Acceptor

In collaboration with the Xue and Zhao groups from Nankai University, we describe a mechanistically unusual reaction to effect oxidative coupling of alkenes and arylboronic acids under nickel(0) catalysis, appearing today in a manuscript in Nature Communications. Previously, it has been shown that Ni(0) can oxidative add into alcohol O–H bonds to generate a catalytically active Ni(H)(OR), which is capable of mediating hydroarylation of alkenes. Based on careful tuning of the directing group, ligand, and hydrogen acceptor (an electron-poor alkene), we find that this pathway can be perturbed to instead give oxidative Heck products. The reaction is highly regioselective, even with challenging 1,2-disubstituted alkene substrates. Congrats to all of the authors.

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