Cascade Intramolecular Prins/Friedel–Crafts Cyclization for the Synthesis of 4-Aryl-tetralin-2-ols and 5-Aryl-tetrahydro-5H-benzo[7]annulen-7-ols

Submitting author affiliation:
Fudan University, Shanghai, China

Beilstein Arch. 2021, 202117.

Published 08 Mar 2021

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Treatment of 2-(2-vinylphenyl)acetaldehydes or 3-(2-vinylphenyl)propanals with BF3×Et2O results in 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-aryl-tetralin-2-ol and 5-aryl-tetrahydro-5H-benzo[7]annulen-7-ol derivatives.

Keywords: Prins/Friedel–Crafts; cascade; 4-aryl-tetralin-2-ol  

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Zheng, J.; Meng, S.; Wang, Q. R. Beilstein Arch. 2021, 202117. doi:10.3762/bxiv.2021.17.v1

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