A Visible Light Photoredox Catalysed Radical Pictet-Spengler Reaction*
Theerada Seehamongkol A , Tyra H. Horngren A , Mohammed A. M. Alhajji A , Joshua Almond-Thynne B , Milena L. Czyz A , Anthony J. Barrett B and Anastasios Polyzos A C D
+ Author Affiliations
- Author Affiliations
A School of Chemistry, The University of Melbourne, Melbourne, Vic. 3010, Australia.
B Department of Chemistry, Imperial College, South Kensington, London SW7 2AY, UK.
C CSIRO Manufacturing, Research Way, Clayton, Vic. 3168, Australia.
D Corresponding author. Email: anastasios.polyzos@unimelb.edu.au
Australian Journal of Chemistry 73(3) 189-194 https://doi.org/10.1071/CH19423
Submitted: 1 September 2019 Accepted: 1 October 2019 Published: 22 November 2019
Abstract
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.
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