Dearomatization of Aromatic Compounds: A Decade Review

Dearomatization offers an efficient strategy for directly converting arenes into cyclic molecules. In this review, we discuss representative examples of dearomatization reactions through five modes: (1) radical dearomatization, (2) halofunctionalization and dearomatization, in which three-membered intermediates were frequently involved, (3) nucleophilic dearomatization mainly about electron-rich arenes, (4) oxidative dearomatization, and (5) reductive dearomatization. Compared to heteroarenes, simple benzene arenes are more challenging to participate in dearomatization reactions. In recent years, fewer reports have focused on benzene. Heteroarenes, which are inherently electron-rich or easily activated, tend to undergo dearomatization reactions more readily. This review highlights a decade of progress in dearomatization of arenes, including indoles, benzofurans, benzothiophenes, thiophenes, furans, naphthols, naphthalenes, quinolines, pyridines, nitrobenzenes, and benzenes. It also analyzes their mechanisms and strategies. We hope this will aid future research in this field.

Abstract

Dearomatization offers an efficient strategy for directly converting arenes into cyclic molecules. In this review, we discuss representative examples of dearomatization reactions through five modes: (1) radical dearomatization, (2) halofunctionalization-dearomatization, in which three-membered intermediates were frequently involved, (3) nucleophilic dearomatization, mainly about electron-rich arenes, (4) oxidative dearomatization, and (5) reductive dearomatization. Compared to heteroarenes, simple benzene arenes are more challenging to participate in dearomatization reactions. In recent years, fewer reports have focused on benzene. Heteroarenes, which are inherently electron-rich or easily activated, tend to undergo dearomatization reactions more readily. This review highlights a decade of progress in dearomatization of arenes, including indoles, benzofurans, benzothiophenes, thiophenes, furans, naphthols, naphthalenes, quinolines, pyridines, nitrobenzenes, and benzenes. It also analyzes their mechanisms and strategies. We hope this will aid future research in this field.

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