Photoelectrochemical C−H Alkylation of Heteroarenes with Organotrifluoroborates

• Published in: Angewandte Chemie International Edition Vol. 58; no. 14; pp. 4592 - 4595
• Main Authors: Yan, Hong, Hou, Zhong‐Wei, Xu, Hai‐Chao
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 26.03.2019; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Alkylation; Catalysis; Chemistry; Chemistry, Multidisciplinary; C−H alkylation; electrochemistry; Organic chemistry; oxidation; Oxidizing agents; photoelectrochemistry; Photoredox catalysis; Physical Sciences; radical reactions; Science & Technology; SYSTEM; ORGANIC-MOLECULES; photoelectrochemistry; electrochemistry; oxidation; radical reactions; POTENTIALS; ELECTROCHEMICAL OXIDATION; PHOTOREDOX CATALYSIS; STRATEGIES; FUNCTIONALIZATION; RADICALS; GENERATION; C-H alkylation; CARBOXYLIC-ACIDS; C−H alkylation
• ISSN: 1433-7851; 1521-3773; 1521-3773
• DOI: 10.1002/anie.201814488

A photoelectrochemical method for the C−H alkylation of heteroarenes with organotrifluoroborates has been developed. The merger of electrocatalysis and photoredox catalysis provides a chemical oxidant‐free approach for the generation and functionalization of alkyl radicals from organotrifluoroborates. A variety of heteroarenes were functionalized using primary, secondary, and tertiary alkyltrifluoroborates with excellent regio‐ and chemoselectivity. A radical approach: A photoelectrochemical method has been developed for the C−H alkylation of heteroarenes with organotrifluoroborates under oxidant‐free conditions. A variety of heteroarenes can be functionalized with primary, secondary, and tertiary alkyl groups with excellent regio‐ and chemoselectivity.