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-苯基-1-萘酰胺的分子内脱氢光环化反应

Intramolecular Dehydrogenative Photocyclization of -Phenyl-1-naphthamides.

作者信息

Li Hao-Yuan, Niu Xiaoying, Zhang Shan-Shan, Shen Shigang, Meng Qing-Yuan, Yang Xiu-Long

机构信息

Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, State Key Laboratory of New Pharmaceutical Preparations and Excipients, Hebei Research Center of the Basic Discipline of Synthetic Chemistry, Key Laboratory of Chemical Biology of Hebei Province (22567635H), College of Chemistry and Materials Science, Hebei University, Baoding 071002, P. R. China.

Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China.

出版信息

Org Lett. 2024 Jun 28;26(25):5364-5369. doi: 10.1021/acs.orglett.4c01805. Epub 2024 Jun 14.

Abstract

Here, we explore a dehydrogenative 6π photocyclization method for -substituted naphthalene carboxamides, which can be conducted in air. This method employs DMSO as both the reaction solvent and oxidant while also stabilizing the excited state of the substrate. Furthermore, the addition of photosensitizer enables the reaction to proceed under a 440-445 nm LED source energy transfer. The proposed mechanism is initially validated through DFT calculations.

摘要

在此,我们探索了一种用于α-取代萘甲酰胺的脱氢6π光环化方法,该方法可在空气中进行。此方法采用二甲基亚砜作为反应溶剂和氧化剂,同时还能稳定底物的激发态。此外,添加光敏剂可使反应在440 - 445纳米发光二极管光源能量转移下进行。所提出的机理最初通过密度泛函理论计算得到验证。

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