Abstract
In this report, we demonstrate that visible-light-induced thiourea photoacids catalyze C-C bond-forming reactions. 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. Mechanistic studies show that light is required for reaction initiation.
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