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通过非活化芳烃的电化学还原氢芳基化实现脱芳构化环化/螺环化

Dearomative Cyclization/Spirocyclization via Electrochemical Reductive Hydroarylation of Nonactivated Arenes.

作者信息

Wu Yi-Miao, Ma Xian-Li, Li Fang-Yao, Huang Chun-Chan, Gao Lei, Zhang Ye, Pan Ying-Ming, He Mu-Xue, Mo Zu-Yu

机构信息

Guangxi Key Laboratory of Drug Discovery and Optimization, Guangxi Engineering Research Center for Pharmaceutical Molecular Screening and Druggability Evaluation, Key Laboratory of Medical and Translational Medicine, School of Pharmacy, Guilin Medical University, Guilin 541199, People's Republic of China.

School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, People's Republic of China.

出版信息

Org Lett. 2024 Oct 25;26(42):8993-8998. doi: 10.1021/acs.orglett.4c02862. Epub 2024 Oct 14.

DOI:10.1021/acs.orglett.4c02862
PMID:39400289
Abstract

An electrochemical cyclization/spirocyclization hydroarylation via reductive dearomatization of a series of nonactivated arenes including -substituted indoles, indole-3-carboxamide derivatives, and iodo-substituted benzamides is described. This protocol boasts high atom efficiency, broad substrate applicability, and excellent selectivity. Utilizing a simple undivided cell, various nonactivated arenes undergo cyclization/spirocyclization through the intramolecular addition of aryl radicals to an aromatic ring, yielding 50 indolines, spirocyclizative hydroarylation products, and phenanthridinones.

摘要

描述了一种通过一系列未活化芳烃(包括α-取代吲哚、吲哚-3-甲酰胺衍生物和碘代苯甲酰胺)的还原脱芳构化进行的电化学环化/螺环化氢芳基化反应。该方法具有高原子效率、广泛的底物适用性和出色的选择性。利用简单的无隔膜电池,各种未活化芳烃通过芳基自由基分子内加成到芳环上进行环化/螺环化反应,生成50种二氢吲哚、螺环化氢芳基化产物和菲啶酮。

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