Photoacid catalysis has recently emerged as a powerful tool for organic synthesis. In this presentation, we will discuss a visible-light-induced thiourea photoacid catalyzed C–C bond-forming reaction. Upon photoirradiation, Schreiner’s thiourea [(N,N′-bis[3,5-bis(trifluoromethyl)phenyl]-thiourea] catalyzes the double Friedel–Crafts addition of indoles to aldehydes and isatins to form the corresponding triarylmethanes and 3,3′-diarylindolin-2-ones. This protocol is amenable to a wide range of aldehyde and isatin electrophiles, as well as a variety of electronically diverse indoles. A novel photoacid catalyst for the formation of C–O bonds will also be discussed. Using 10 mol% 6-bromo-2-naphthol enables the photo-induced acetalization of aldehydes with a range of alcohols. Mechanistic studies will also be discussed.

Photoacid-catalyzed C–C and C–O bond-formation

ACS Spring 2022

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