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镍催化的未活化脂肪族 C-H 键与炔烃的加成型烯丙基化反应:多取代 γ-丁内酯的简洁合成路线。

Nickel-Catalyzed Addition-Type Alkenylation of Unactivated, Aliphatic C-H Bonds with Alkynes: A Concise Route to Polysubstituted γ-Butyrolactones.

机构信息

Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, and State Key Laboratory of Biotherapy, West China Medical School, Sichuan University, 29 Wangjiang Road, Chengdu 610064, China.

出版信息

Org Lett. 2015 May 15;17(10):2546-9. doi: 10.1021/acs.orglett.5b01128. Epub 2015 Apr 30.

Abstract

Through the nickel-catalyzed chelation-assisted C-H bond activation strategy, the addition-type alkenylation of unreactive β-C(sp(3))-H bonds of aliphatic amides with internal alkynes is developed for the first time to produce γ,δ-unsaturated carboxylic amide derivatives. The resulting alkenylated products can further be transformed into polysubstituted γ-butyrolactones with pyridinium chlorochromate (PCC).

摘要

通过镍催化的螯合辅助 C-H 键活化策略,首次开发了脂肪族酰胺中β-C(sp(3))-H 键的加成型烯基化反应,用于与内部炔烃反应生成γ,δ-不饱和羧酸酰胺衍生物。得到的烯基化产物可以进一步用吡啶氯铬酸盐(PCC)转化为多取代的γ-丁内酯。

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