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Cascade intramolecular Prins/Friedel-Crafts cyclization for the synthesis of 4-aryltetralin-2-ols and 5-aryltetrahydro-5H-benzo[7]annulen-7-ols.

ABSTRACT: The treatment of 2-(2-vinylphenyl)acetaldehydes or 3-(2-vinylphenyl)propanals with BF₃·Et₂O results in an intramolecular Prins reaction affording intermediary benzyl carbenium ions, which are then trapped by a variety of electron-rich aromatics via Friedel-Crafts alkylation. This cascade Prins/Friedel-Crafts cyclization protocol paves an expedient path to medicinally useful 4-aryltetralin-2-ol and 5-aryltetrahydro-5H-benzo[7]annulen-7-ol derivatives.

SUBMITTER: Zheng J

PROVIDER: S-EPMC8239259 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Remarkably mild and efficient intramolecular Friedel-Crafts cyclization catalyzed by In(III).

Project description:[structure: see text]. Indium(III) salts were found to be highly effective catalysts for the intramolecular Friedel-Crafts reaction of simple allylic bromides and arenes. In(III) salts appear to be the most general and possess unique halophilic properties as a Lewis acid for this reaction among the catalysts evaluated to date. Deactivated arenes possessing chloride, bromide, and fluoride underwent smooth reaction when activated by InCl3.

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