Lu Lingyi, Sui Jing, Huang Shanshan, Xiong Biao, Zeng Xiaobao, Qiu Xiaodong, Zhang Yanan
Nantong Key Laboratory of Small Molecular Drug Innovation, School of Pharmacy, Nantong University, 19 Qixiu Road, Nantong 226001, China.
Org Lett. 2023 Nov 3;25(43):7800-7804. doi: 10.1021/acs.orglett.3c02955. Epub 2023 Oct 24.
Chemo and regioselective dialkylation of alkene is an efficient protocol for constructing useful chemicals, but challenges remain in the unrestricted application of alkylating reagents. Alkyl bromide belongs to the easy-to-access and operable alkyl electrophiles that can be used in reductive coupling with alkenes. Here, we reported convenient strategies for dialkylcyclization and homodialkylation of unactivated β,γ- and γ,δ-unsaturated alkenyl amides with 1,3-dibromoalkanes or primary alkyl bromides under nickel-catalyzed reductive conditions that exhibited high regioselectivity and functional-group tolerance.
烯烃的化学选择性二烷基化是构建有用化学品的有效方法，但烷基化试剂的无限制应用仍存在挑战。溴代烷属于易于获取和操作的烷基亲电试剂，可用于与烯烃的还原偶联反应。在此，我们报道了在镍催化的还原条件下，未活化的β,γ-和γ,δ-不饱和烯基酰胺与1,3-二溴代烷或伯烷基溴进行二烷基环化和同二烷基化的简便策略，该策略具有高区域选择性和官能团耐受性。
