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通过钯催化和可见光光氧化还原催化相结合实现胺的氧化还原中性 α-烯丙基化反应。

Redox-neutral α-allylation of amines by combining palladium catalysis and visible-light photoredox catalysis.

机构信息

CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University (CCNU), 152 Luoyu Road, Wuhan, Hubei 430079 (China) http://chem-xiao.ccnu.edu.cn/

出版信息

Angew Chem Int Ed Engl. 2015 Jan 26;54(5):1625-8. doi: 10.1002/anie.201409999. Epub 2014 Dec 10.

Abstract

An unprecedented α-allylation of amines was achieved by combining palladium catalysis and visible-light photoredox catalysis. In this dual catalysis process, the catalytic generation of allyl radical from the corresponding π-allylpalladium intermediate was achieved without additional metal reducing reagents (redox-neutral). Various allylation products of amines were obtained in high yields through radical cross-coupling under mild reaction conditions. Moreover, the transformation was applied to the formal synthesis of 8-oxoprotoberberine derivatives which show potential anticancer properties.

摘要

通过钯催化和可见光光氧化还原催化相结合,实现了胺的空前的α-烯丙基化。在这个双催化过程中,通过相应的π-烯丙基钯中间体催化生成烯丙基自由基,而无需额外的金属还原试剂(氧化还原中性)。在温和的反应条件下,通过自由基交叉偶联,各种胺的烯丙基化产物以高产率得到。此外,该转化被应用于具有潜在抗癌活性的 8-氧代原小檗碱衍生物的形式合成。

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