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手性双/全氟烷基化 β-酮酯通过协同光氧化还原/镍催化实现。

Enantioselective Di-/Perfluoroalkylation of β-Ketoesters Enabled by Cooperative Photoredox/Nickel Catalysis.

机构信息

Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis, Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University , 152 Luoyu Road, Wuhan, Hubei 430079, P. R. China.

State Key Laboratory of Applied Organic Chemistry, Lanzhou University , Lanzhou 730000, China.

出版信息

Org Lett. 2018 Jan 19;20(2):461-464. doi: 10.1021/acs.orglett.7b03826. Epub 2018 Jan 9.

Abstract

Efficient and enantioselective radical difluoroalkylation and perfluoroalkylation reactions of β-ketoesters were successfully developed through an asymmetric photoredox and nickel catalysis cascade. This protocol provides R-containing quaternary stereocenters in up to 67% yield and 95:5 er with ethyl iododifluoroacetate and perfluoroalkyl iodides (CFI and CFI) as radical sources under extremely mild conditions.

摘要

通过不对称光氧化还原和镍催化级联反应,成功开发了β-酮酯的高效和对映选择性自由基二氟烷基化和全氟烷基化反应。该方案在极其温和的条件下,以乙基碘二氟乙酸酯和全氟碘代烷(CFI 和 CFI)作为自由基源,提供了高达 67%产率和 95:5er 的含有 R 的季立体中心。

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