Seminar Abstract:
Organosulfonium salts have recently seen an increase in utility as a handle towards a wide variety of powerful synthetic transformations. This is highlighted by the reactivity of thianthrenium salts and derivatives across transition-metal (TM) catalysis, photochemistry, electrochemistry, and radical polar crossover (RPC) reactions. Aryl sulfonium salt synthesis (e.g., thianthrenium and phenothiazinium species) has been extensively developed relative to their alkyl variants, which are highly limited when it comes to their incorporation into 20, 30, and even complex structures that include preinstalled directing groups. I propose that the facile synthesis of phenothiazinium amine salts as well as their photoinduced homolytic cleavage of the sulfilimine bond can be utilized to both exploit the high reactivity of the nitrogen centered radical (NCR) intermediate and consequently trap the resulting radical species with the persistent phenothiazinium radical cation. The overall transformation would result in the displacement of phenothiazinium group via photoinduced activation, providing access to a wide variety of complex phenothiazinium salt derivatives as a handle towards additional valuable products.
