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

Pavlo Nikolaienko; Marc Jentsch; Ajit P Kale; Yunfei Cai; Magnus Rueping

doi:10.1002/chem.201806092

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

Chemistry. 2019 May 23;25(29):7177-7184. doi: 10.1002/chem.201806092. Epub 2019 May 2.

Authors

Pavlo Nikolaienko¹, Marc Jentsch², Ajit P Kale¹, Yunfei Cai¹, Magnus Rueping^{1

2}

Affiliations

¹ KAUST Catalysis Center (KCC), King Abdullah University of Science and Technology (KAUST), Thuwal, 23955-6900, Saudi Arabia.
² Institute of Organic Chemistry, RWTH-Aachen University, Landoltweg 1, 52074, Aachen, Germany.

PMID: 30861204
DOI: 10.1002/chem.201806092

Abstract

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.

Keywords: 1,5-HAT; amination; electrosynthesis; flow electrolysis; pyrrolidines.