Straightforward Synthesis of Dihydrobenzo[a]fluorenes through Au(I)-Catalyzed Formal [3 + 3] Cycloadditions

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...

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Bibliographic Details
Published in:Organic letters 2012-09, Vol.14 (18), p.4778-4781
Main Authors: García-García, Patricia, Rashid, Muhammad A, Sanjuán, Ana M, Fernández-Rodríguez, Manuel A, Sanz, Roberto
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Catalysis
Cycloaddition Reaction
Fluorenes - chemical synthesis
Fluorenes - chemistry
Gold - chemistry
Molecular Structure
Stereoisomerism
Styrenes - chemistry
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol3020682