Abstract
Aerobic oxidative dehydrogenation reactions of benzylamines to imines were studied and the efficiencies of various ground- and excited state quinone organocatalysts were compared. Long wave-absorbing anthraquinones readily catalyze the aerobic photodehydrogenation of primary and secondary benzylamines to benzylidenebenzylamines with high rate and selectivity, and the reaction mechanism was ...
Abstract
Aerobic oxidative dehydrogenation reactions of benzylamines to imines were studied and the efficiencies of various ground- and excited state quinone organocatalysts were compared. Long wave-absorbing anthraquinones readily catalyze the aerobic photodehydrogenation of primary and secondary benzylamines to benzylidenebenzylamines with high rate and selectivity, and the reaction mechanism was studied by laser flash photolysis. Further, branched alpha-benzyl dibenzyl-amines undergo a regioselective photocatalytic dehydrogenation to branched aldimines, which can efficiently be converted into cis-1,3-diaryl tetrahydro-isoquinolines through diastereoselective super acid-mediated Pictet-Spengler cyclizations.
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