Friedel–Crafts Alkylation of Indoles with Aldehydes/Ketones Catalyzed by Bromodiarylethene-Based Photoacid Generators

Abstract

Diarylethenes (DAEs) with a bromine atom at the ring-closing position catalyze C–C bonding reactions induced by UV or sunlight. Upon photo-irradiation, bromodiarylethenes undergo 6π-electrocyclization (6π-EC), followed by the release of an acid species that 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 applicable to a wide spectrum of aldehydes and isatins, as well as chalcones as electrophiles. Acid or oxidant-sensitive functional groups, such as ferrocene, 4-methoxyphenyl, thiophene, pyrrole are tolerated. Mechanistic studies show that light is needed to initiate the reaction.

Key words

aldehydes - catalysis - diarylethenes - diindolylmethanes - Friedel–Crafts alkylation - Lewis acid - photoacid generators - photochemistry

Publikationsverlauf

Eingereicht: 16. Januar 2024

Angenommen nach Revision: 16. Februar 2024

Accepted Manuscript online:
16. Februar 2024

Artikel online veröffentlicht:
06. März 2024

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