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可见光诱导下2-乙炔基苯胺在环境条件下的硒环化反应:简单的溴化铁作为双功能催化剂

Visible-light induced selenocyclization of 2-ethynylanilines under ambient conditions: simple FeBr as a dual-functional catalyst.

作者信息

Huang Binbin, Tang Xinye, Yuan Jiawei, Zhang Mingyu, Luo Zhenyu, Wang Junlei, Lu Caicai

机构信息

Faculty of Arts and Sciences/College of Education for the Future, Beijing Normal University, Zhuhai 519085, China.

School of Chemical Engineering, Guizhou Minzu University, Guiyang 550025, China.

出版信息

Org Biomol Chem. 2024 Jul 31;22(30):6198-6204. doi: 10.1039/d4ob01062k.

Abstract

We report herein a visible-light induced, Fe-catalyzed selenocyclization of 2-ethynylanilines with diselenides under ambient conditions, employing ethyl acetate as a benign solvent with no stoichiometric additive required. The simple iron salt FeBr serves as both a photo-induced LMCT (Ligand-to-Metal Charge Transfer) catalyst and a Lewis acid catalyst to promote the desired transformation in a sustainable manner, enabling the facile synthesis of diverse 3-selenylindoles with extended substitution patterns. Moreover, gram-scale reactions and late-stage functionalization of bioactive molecules further highlight the synthetic practicality of this method.

摘要

我们在此报告,在环境条件下,以乙酸乙酯作为良性溶剂且无需化学计量添加剂,可见光诱导、铁催化2-乙炔基苯胺与二硒化物发生硒环化反应。简单的铁盐FeBr既作为光诱导配体-金属电荷转移(LMCT)催化剂,又作为路易斯酸催化剂,以可持续的方式促进所需的转化,能够轻松合成具有扩展取代模式的多种3-硒代吲哚。此外,克级规模反应以及生物活性分子的后期官能团化进一步突出了该方法的合成实用性。

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