Wang Siyu, Zheng Lianyou, Wang Shutao, Ning Shulin, Zhang Zhuoqi, Xiang Jinbao
The Center for Combinatorial Chemistry and Drug Discovery, School of Pharmaceutical Sciences, Jilin University, 1266 Fujin Road, Changchun, Jilin 130021, P. R. China.
Beilstein J Org Chem. 2021 Oct 1;17:2505-2510. doi: 10.3762/bjoc.17.167. eCollection 2021.
A base- and catalyst-free C(sp)-H allylic alkylation of 2-alkylpyridines with Morita-Baylis-Hillman (MBH) carbonates is described. A plausible mechanism of the reaction might involve a tandem S2' type nucleophilic substitution followed by an aza-Cope rearrangement. Various alkyl substituents on 2-alkylpyridines were tolerated in the reaction to give the allylation products in 26-91% yields. The developed method provides a straightforward and operational simple strategy for the allylic functionalization of 2-alkypyridine derivatives.
本文描述了一种2-烷基吡啶与森田-贝利斯-希尔曼（MBH）碳酸酯的无碱无催化剂的C(sp)-H烯丙基烷基化反应。该反应可能的机理或许涉及串联的S2'型亲核取代反应，随后是氮杂-Cope重排。2-烷基吡啶上的各种烷基取代基在该反应中均能耐受，可得到产率为26%-91%的烯丙基化产物。所开发的方法为2-烷基吡啶衍生物的烯丙基官能化提供了一种直接且操作简便的策略。
