An unprecedented copper-catalyzed intramolecular radical cyclization was developed for the synthesis of 3-hydroxypyrroloindoline skeletons in excellent yields. The 3-hydroxyl group was introduced by trapping the radical intermediate with molecular oxygen or TEMPO. This process represents a unique radical oxidation pathway for tryptamine/tryptophan derivatives and allows a rapid biomimetic synthesis of natural product protubonine A.

An operationally simple photochemical strategy for the direct arylation of oxindoles with (hetero)aryl halides in the absence of both transition metals and photoredox catalysts has been developed.

The thiophenol was discovered to form an EDA complex with iodobenzene through halogen bonding interactions upon treatment with KOH. A direct photochemical thiolation of C(sp3)–H bonds containing etheric, allylic, and...