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

作者:Hanna Luke E; Harris Michael R; Domon Kenji; Jarvo Elizabeth R*
来源:Organic Letters, 2017, 19(23): 6304-6307.
DOI:10.1021/acs.orglett.7b03049

摘要

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

  • 出版日期2017-12-1