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光氧化还原/铁双催化实现的酰基氮烯与炔烃的[4+2]环化反应

Photoredox/Iron Dual-Catalysis-Enabled [4 + 2] Cyclization of Acyl Nitrene with Alkynes.

作者信息

Xie Shimin, Tang Shuwang, Hou Ming, Xie Wenlin, Guan Meng, Bai Tianwen, He Linli, Qiu Guanyinsheng

机构信息

School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, Hunan, China.

College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, Zhejiang, China.

出版信息

Org Lett. 2024 Dec 27;26(51):11134-11139. doi: 10.1021/acs.orglett.4c04069. Epub 2024 Dec 13.

Abstract

In this work, the annulation of acyl nitrene with alkynes is reported under photoredox/iron dual-catalysis for the synthesis of a series of isoquninalin-2-ones. The reaction is featured with a high reaction regioselectivity and good reaction generality. In particular, the resulting isoquinalin-2-ones could be structurally elaborated into several biologically interesting scaffolds. Mechanism investigation suggests that the reaction was ascribed to a formal [4 + 2] cyclization. It is believed that this reaction represents an initial example of preparing isoquinolin-1-ones from ferric peroxyl-catalyzed nitrene insertion.

摘要

在这项工作中,报道了在光氧化还原/铁双催化下酰基氮烯与炔烃的环化反应,用于合成一系列异喹啉-2-酮。该反应具有高反应区域选择性和良好的反应通用性。特别地,所得的异喹啉-2-酮可以在结构上进一步衍生为几种具有生物学意义的骨架。机理研究表明该反应归因于形式上的[4+2]环化。据信,该反应代表了通过铁过氧催化的氮烯插入制备异喹啉-1-酮的首个实例。

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