Electrochemical and Scalable Dehydrogenative C(sp3)−H Amination via Remote Hydrogen Atom Transfer in Batch and Continuous Flow

• Published in: Chemistry : a European journal Vol. 25; no. 29; pp. 7177 - 7184
• Main Authors: Nikolaienko, Pavlo, Jentsch, Marc, Kale, Ajit P., Cai, Yunfei, Rueping, Magnus
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 23.05.2019; Wiley Subscription Services, Inc
• Subjects: 1,5-HAT; Amination; Chemistry; Chemistry, Multidisciplinary; Continuous flow; Dehydrogenation; Electrochemistry; electrosynthesis; flow electrolysis; Physical Sciences; pyrrolidines; Science & Technology; NITROAMINE RADICALS; REAGENT; electrosynthesis; OMARIGLIPTIN; INTRAMOLECULAR FUNCTIONALIZATION; flow electrolysis; 1,5-HAT; H FUNCTIONALIZATION; AMIDYL; pyrrolidines; amination; GENERATION; CYCLIZATION; ANODIC-OXIDATION
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201806092

A hydrogen atom transfer‐directed electrochemical intramolecular C−H amination has been developed in which the N‐radical species are generated at the anode, and the base required for the reaction is generated at the cathode. A broad range of valuable pyrrolidines were prepared in good yields and with high chemoselectivity. The reaction was easily scaled up in both batch and continuous flow systems. A hydrogen atom transfer‐directed electrochemical intramolecular C−H amination has been developed in which the N‐radical species are generated at the anode, and the base required for the reaction is generated at the cathode. A broad range of valuable pyrrolidines were prepared in good yields and with high chemoselectivity. The reaction was easily scaled up in both batch and continuous flow systems.