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Nickel-Catalyzed Hydrogenolysis and Conjugate Addition of 2‑(Hydroxymethyl)pyridines via Organozinc Intermediates

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journal contribution
posted on 14.11.2017, 15:11 by Luke E. Hanna, Michael R. Harris, Kenji Domon, Elizabeth R. Jarvo
2-Hydroxymethylpyridines undergo nickel-catalyzed hydrogenolysis upon activation with a chlorophosphate. Reactions employ diethylzinc and are proposed to proceed through secondary benzylzinc reagents. Quenching with deuteromethanol provides straightforward incorporation of a deuterium label in the benzylic position. Intramolecular conjugate additions with α,β-unsaturated esters are also demonstrated and support the intermediacy of a benzylzinc complex.