title: 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.
authors.affiliation: Department of Chemistry, Boston University, Boston, Massachusetts 02215, USA.
authors.forename: David B
authors.initials: DB
authors.lastname: Freeman
authors.forename: Laura
authors.initials: L
authors.lastname: Furst
authors.forename: Allison G
authors.initials: AG
authors.lastname: Condie
authors.forename: Corey R J
authors.initials: CR
authors.lastname: Stephenson
mesh_terms: D000478:Alkylation; D002384:Catalysis; D007097:Imines / Q000737:chemistry*; D008027:Light; D015394:Molecular Structure; D010084:Oxidation-Reduction; D055668:Photochemical Processes; D011522:Protons
chemical_list: D007097:Imines; D011522:Protons