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. 2013 Jul 3;135(26):9588-91.
doi: 10.1021/ja4031616. Epub 2013 Jun 19.

Anti-Markovnikov hydroamination of alkenes catalyzed by an organic photoredox system

Tien M Nguyen  1 , David A Nicewicz
Affiliations

Anti-Markovnikov hydroamination of alkenes catalyzed by an organic photoredox system

Tien M Nguyen et al. J Am Chem Soc. .

Abstract

Herein we report a metal-free method for the direct anti-Markovnikov hydroamination of unsaturated amines. Irradiation of the amine substrates with visible light in the presence of catalytic quantities of easily synthesized 9-mesityl-10-methylacridinium tetrafluoroborate and thiophenol as a hydrogen-atom donor furnished the nitrogen-containing heterocycles with complete regiocontrol. Two examples of intermolecular anti-Markovnikov alkene hydroamination are also disclosed.

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Conflict of interest statement

Funding Sources

The authors declare no competing financial interests.

Figures

Figure 1
Figure 1
Catalytic Anti-Markovnikov Intramolecular Hydroamination
Scheme 1
Scheme 1
Working Mechanism for Direct Anti-Markovnikov Hydroamination of Alkenes
See this image and copyright information in PMC

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