Department of Chemistry, University of California , Irvine, California 92697-2025, United States.
Org Lett. 2017 Dec 1;19(23):6304-6307. doi: 10.1021/acs.orglett.7b03049. Epub 2017 Nov 14.
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.
2-羟甲基吡啶在膦酰氯激活下发生镍催化氢解反应。反应采用二乙基锌，并被提议通过二级苄基锌试剂进行。用氘代甲醇猝灭可直接在苄位引入氘代标记。还证明了与α,β-不饱和酯的分子内共轭加成反应，并支持了苄基锌络合物的中间体的存在。
