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

Pavlo Nikolaienko, Marc Jentsch, Ajit P. Kale, Yunfei Cai, Magnus Rueping^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

39 Scopus citations

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.

Original language	English (US)
Pages (from-to)	7177-7184
Number of pages	8
Journal	Chemistry - A European Journal
Volume	25
Issue number	29
DOIs	https://doi.org/10.1002/chem.201806092
State	Published - May 23 2019

Keywords

1,5-HAT
amination
electrosynthesis
flow electrolysis
pyrrolidines

ASJC Scopus subject areas

Catalysis
General Chemistry
Organic Chemistry

Access to Document

10.1002/chem.201806092

Cite this

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

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",

author = "Pavlo Nikolaienko and Marc Jentsch and Kale, {Ajit P.} and Yunfei Cai and Magnus Rueping",

note = "Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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AU - Jentsch, Marc

AU - Kale, Ajit P.

AU - Cai, Yunfei

AU - Rueping, Magnus

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AB - 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.

KW - 1,5-HAT

KW - amination

KW - electrosynthesis

KW - flow electrolysis

KW - pyrrolidines

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