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

ABSTRACT: 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 ?,?-unsaturated esters are also demonstrated and support the intermediacy of a benzylzinc complex.

SUBMITTER: Hanna LE 

PROVIDER: S-EPMC6402844 | biostudies-literature | 2017 Dec

REPOSITORIES: biostudies-literature

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

Hanna Luke E LE   Harris Michael R MR   Domon Kenji K   Jarvo Elizabeth R ER  

Organic letters 20171114 23

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. ...[more]

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