1350895-84-9Relevant academic research and scientific papers
Carbon Nitride-Catalyzed Photoredox Sakurai Reactions and Allylborations
M?hlmann, Lennart,Blechert, Siegfried
, p. 2825 - 2829 (2014)
Within the last couple of years, the photocatalytic, oxidative C-C coupling has grown to a well-established methodology, especially for the modification of aryl-substituted tetrahydroisoquinoline derivatives. However, until now, this reaction is mainly restricted to the usage of strong nucleophiles like nitroalkanes, cyanides, enamines, phosphonates and malonates. Within this publication we present an extension of such a method towards the application of weaker nucleophiles, namely allylstannanes, allylsilanes and allylboranes. Therefore, a very simple protocol was invented, using heterogeneous mesoporous graphitic carbon nitride (mpg-C3N4) as catalyst and air as oxidizing agent, leading to high yields for a broad range of substrates.
Functionally diverse nucleophilic trapping of iminium intermediates generated utilizing visible light
Freeman, David B.,Furst, Laura,Condie, Allison G.,Stephenson, Corey R. J.
supporting information; experimental part, p. 94 - 97 (2012/02/16)
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.
