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. 2012 Jan 6;14(1):94-7.
doi: 10.1021/ol202883v. Epub 2011 Dec 8.

Functionally diverse nucleophilic trapping of iminium intermediates generated utilizing visible light

David B Freeman  1 , Laura Furst, Allison G Condie, Corey R J Stephenson
Affiliations

Functionally diverse nucleophilic trapping of iminium intermediates generated utilizing visible light

David B Freeman et al. Org Lett. .

Abstract

Our previous studies into visible-light-mediated aza-Henry reactions demonstrated that molecular oxygen played a vital role in catalyst turnover as well as the production of base to facilitate the nucleophilic addition of nitroalkanes. Herein, improved conditions for the generation of iminium ions from tetrahydroisoquinolines that allow for versatile nucleophilic trapping are reported. The new conditions provide access to a diverse range of functionality under mild, anaerobic reaction conditions as well as mechanistic insights into the photoredox cycle.

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Figures

Figure 1
Figure 1
Physical properties of amino radical cations and their potential for diversification under visible light-mediated photoredox catalysis
Figure 2
Figure 2
Alkynylation coupled with photoredox catalysis
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