Electrochemical phenothiazination of naphthylamines and its application in photocatalysis

N-Phenylphenothiazine as an inexpensive, highly reductive and oxygen tolerant organophotocatalyst has exhibited potential in various challenging photochemical transformations. Here we report a general and straightforward method to access structurally diverse N-phenylphenothiazine derivatives by means of a novel electrochemical tool. The introduction of a 2-naphthylamine moiety with an extended pi-system and an amine group led to the variation of spectral characterization. Photochemical verification experiments demonstrated that the formed N-arylation products with good efficacy and chemo/site-control displayed competitive catalytic activity in challenging transformations.

Automated summary

A novel electrochemical approach was developed to access structurally varied N-phenylphenothiazine derivatives with altered spectral characteristics. The introduction of a 2-naphthylamine moiety led to changes in the spectral properties and competitive catalytic activity of the formed N-arylation products in challenging transformations.