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Updated: May 19, 2026

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Published on: June 10, 2021
Straightforward synthesis of dihydrobenzo[a]fluorenes through Au(I)-catalyzed formal [3 + 3] cycloadditions
Patricia García-García1, Muhammad A Rashid, Ana M Sanjuán
1Área de Química Orgánica, Departamento de Química, Facultad de Ciencias, Universidad de Burgos, Pza. Misael Bañuelos s/n, 09001-Burgos, Spain.
Abstract:
Dihydrobenzo[a]fluorene derivatives have been prepared by a formal intramolecular [3 + 3] cycloaddition of o-alkynylstyrenes bearing a secondary alkyl group at the β-position of the styrene moiety. The process, catalyzed by a cationic gold(I) complex, involves a 1,2-hydride migration as the key step. 6,11-Dihydro-5H-benzo[a]fluorenes could be obtained from the initially generated 6,6a-dihydro-5H-benzo[a]fluorenes by subsequent heating of the reaction mixture under gold(I) or Brønsted acid catalysis or directly by conducting the reactions at high temperature.
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