Electrochemical Oxidative C−H Amination of Phenols: Access to Triarylamine Derivatives

• Published in: Angewandte Chemie International Edition Vol. 57; no. 17; pp. 4737 - 4741
• Main Authors: Tang, Shan, Wang, Siyuan, Liu, Yichang, Cong, Hengjiang, Lei, Aiwen
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 16.04.2018; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Amination; Catalysts; Chemistry; Chemistry, Multidisciplinary; cross-coupling; C−H functionalization; Dehydrogenation; Derivatives; Electrochemistry; Electrolysis; heterocyles; Oxidants; Oxidizing agents; Phenols; Physical Sciences; Science & Technology; CATALYSIS; electrochemistry; ANNULATION; ARENES; MOLECULAR MATERIALS; C-H functionalization; TRANSFER RADICAL POLYMERIZATION; heterocyles; FUNCTIONALIZATION; CROSS-COUPLING REACTIONS; cross-coupling; OXIDANT; DEVICES; amination; N BOND FORMATION; C−H functionalization
• ISSN: 1433-7851; 1521-3773; 1521-3773
• DOI: 10.1002/anie.201800240

Dehydrogenative C−H/N−H cross‐coupling serves as one of the most straightforward and atom‐economical approaches for C−N bond formation. In this work, an electrochemical reaction protocol has been developed for the oxidative C−H amination of unprotected phenols under undivided electrolytic conditions. Neither metal catalysts nor chemical oxidants are needed to facilitate the dehydrogenation process. A series of triarylamine derivatives could be obtained with good functional‐group tolerance. The electrolysis is scalable and can be performed at ambient conditions. Undivided attention: An atom‐economical oxidative C−H amination of unprotected phenols was achieved by an external oxidant‐free electrochemical reaction. Under undivided electrolytic conditions, triarylamine derivatives were produced with high functional‐group tolerance along with H2 generation.