The main scientific objective of my doctoral studies was to demonstrate the potential of the excited-state reactivity of organocatalytic intermediates to develop novel catalytic radical C-C and C-B forming reactions.
In a first example, we harnessed the enhanced oxidative properties of visible-light excited chiral iminium ions and the basic character of their counteranions to promote, through a multisite proton coupled electron transfer, an asymmetric C-H functionalization of toluene and derivatives.
In the second part of my doctoral studies, we employed a nucleophilic dithiocarbonyl anion organocatalyst to activate alkyl electrophiles through an SN2 pathway and acyl and carbamoyl derivatives through a nucleophlic acyl substitution pathway. The ensuing intermediates, upon visible light absorption, generate radicals that have been employed to promote the formation of C-B and C-C bonds.
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