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Synthesis
DOI: 10.1055/a-2270-3973
DOI: 10.1055/a-2270-3973
paper
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 - photochemistrySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2270-3973.
- Supporting Information
Publication History
Received: 16 January 2024
Accepted after revision: 16 February 2024
Accepted Manuscript online:
16 February 2024
Article published online:
06 March 2024
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