Allyl Electrophiles in Conjunctive Cross-Coupling – Paper Now In Press

Team Nickel’s first publication of 2020 is now in press and Angewandte Chemie International Edition. The paper describes the strategic merger of two enabling reactivity modes in organic synthesis: (1) transition-metal-catalyzed allylation, and (2) nickel-catalyzed (three-component) conjunctive cross-coupling of alkenes. This method allows for each of the two alkenyl carbon atoms to engage in C(sp3)–C(sp3) bond formation with two differentiated reaction partners, and allyl moiety and a methyl group. Mechanistically, the success of the reaction hinges upon use of weakly coordinating heterocyclic directing groups that enable dynamic coordination of the alkene from the allyl group to trigger C(sp3)–C(sp3) reductive elimination. Congrats to the whole team, Van, Zi-Qi, Tim, and Joe. Thanks to our valued collaborator Prof. Peng Liu from University of Pittsburgh for key insights regarding DFT calculations.  In case anyone missed it, a pre-print of this work was deposited in ChemRxiv back in August (click here).

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