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可见光诱导亚胺与酸酐的交叉亲电偶联反应合成α-氨基酮

Visible-light induced cross-electrophile coupling of imines and anhydrides to synthesize α-amino ketones.

作者信息

Cao Renxu, Liu Yu, Shi Xiaoxin, Zheng Jun

机构信息

Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, and the School of Pharmacy, East China University of Science and Technology, Shanghai 200237, P. R. China.

出版信息

Chem Commun (Camb). 2023 Aug 31;59(71):10668-10671. doi: 10.1039/d3cc03028h.

Abstract

α-Amino ketones are important motifs in synthetic and medicinal chemistry. Efficient methods to directly access these motifs from feasible precursors are, however, limited. Herein, a visible-light mediated reductive cross-electrophile coupling of readily available imines and anhydrides was developed. Under mild reaction conditions, the umpolung reactivity of diverse imines engaged with anhydrides gives a variety of α-amino ketones with good yields and a broad functional group compatibility. Primary mechanistic studies revealed that this transformation might proceed through a radical-radical cross coupling pathway dominantly.

摘要

α-氨基酮是合成化学和药物化学中的重要结构单元。然而,从可行的前体直接获得这些结构单元的有效方法有限。在此,我们开发了一种可见光介导的、由易得的亚胺和酸酐进行的还原交叉亲电偶联反应。在温和的反应条件下,各种亚胺与酸酐的极性反转反应性能够得到多种α-氨基酮,产率良好且官能团兼容性广泛。初步机理研究表明,这种转化可能主要通过自由基-自由基交叉偶联途径进行。

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