A Visible Light Photoredox Catalysed Radical Pictet-Spengler Reaction*
Theerada Seehamongkol, Tyra H Horngren, Mohammed AM Alhajji, Joshua Almond-Thynne, Milena L Czyz, Anthony J Barrett, Anastasios Polyzos
Australian Journal of Chemistry | CSIRO PUBLISHING | Published : 2020
A methodology for a radical Pictet–Spengler reaction promoted by visible light photoredox catalysis is described. This strategy furnishes tetrahydroisoquinoline derivatives bearing electron poor and electron rich substituents. The reaction proceeds at room temperature and with excellent regioselectivity for the 6-endo intramolecular cyclisation. This radical approach provides a complementary method for the synthesis of the tetrahydroisoquinoline scaffold with substitution patterns inaccessible via established thermal transformations.
Awarded by ARC Industrial Transformation Training Centre Grant
MLC acknowledges the Australian Research Council (ARC) Industrial Transformation Training Centre Post-Doctoral Fellowship; THH acknowledges the University of Melbourne, Melbourne Research Scholarship (MRS); AP acknowledges the University of Melbourne and CSIRO for the joint Establishment Grant and the ARC Industrial Transformation Training Centre Grant (IC1701000020).