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Functionally diverse nucleophilic trapping of iminium intermediates generated utilizing visible light.

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.

SUBMITTER: Freeman DB

PROVIDER: S-EPMC3253246 | biostudies-literature | 2012 Jan

REPOSITORIES: biostudies-literature

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Functionally diverse nucleophilic trapping of iminium intermediates generated utilizing visible light.

Freeman David B DB Furst Laura L Condie Allison G AG Stephenson Corey R J CR

Organic letters 20111208 1

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 ...[more]

PMID: 22148974

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