Phenylphenothiazine expands the reactivity profile of organic photoredox catalysts due to its potential of -2.1 V, that is already at the edge of conventionally used photoredox catalysts. They enable the activation of the completely inert sulfur hexafluoride, for pentafluorosulfanylations of organic compounds. Our photocatalytic approach promises a simple and, unlike other pentasulfanylation methods, a non-toxic and sustainable access to SF<sub>5</sub>-styrenes.<br/>By introducing a dialkylamino substituent as a simple chemical modification, the excited state potential of phenothiazine is shifted up to -3.0 V, bringing this photocatalyst into the region of elemental sodium and making it one of the strongest reductants known in literature. This allows the photoredox catalytic addition of alcohols of non-activated alkyl olefins without the help of an additional reagent.<br/>This highly reducing catalyst can also be used for intramolecular alkoxycyclizations. Together with our research activity with perylene bisimides, this yields a complementary photocatalytic toolbox that allows full control over endo- or exo-trig cyclizations to medicinal-chemical important oxaheterocyclic products.

Using Arylphenothiazines as highly reducing photocatalysts for pentafluorosulfanylations, alkoxylations and alkoxycyclizations

Fall 2022 abstracts, posters, and presentations will launch in mid-September.

ACS Fall 2022

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.