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Brønsted Acid‐Catalyzed Carbocyclization of 2‐Alkynyl Biaryls

Julien Gicquiaud 1 Antoine Hacihasanoğlu 1 Philippe Hermange 1 Jean-Marc Sotiropoulos 2 Patrick Y. Toullec 1, * 
* Corresponding author
1 ISM - Institut des Sciences Moléculaires
2 IPREM - Institut des sciences analytiques et de physico-chimie pour l'environnement et les materiaux
Abstract : Ortho‐alkynyl biaryls react in the presence of catalytic amount of Brønsted acids to give phenanthrenes in high yields under mild conditions. The activity and selectivity of this transformation are governed by the substitution pattern of the diarylalkyne moiety. Selectivity shifts are observed between the carbophilic Lewis and Brønsted acid‐catalyzed cycloisomerization involving alkyne activation.
Keywords : Cycloisomerization Electrophilic activation Phenanthrenes Alkynes Brønsted acid catalysis Phe- nanthrenes Cycloisomeriza- tion
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Julien Gicquiaud, Antoine Hacihasanoğlu, Philippe Hermange, Jean-Marc Sotiropoulos, Patrick Y. Toullec. Brønsted Acid‐Catalyzed Carbocyclization of 2‐Alkynyl Biaryls. Advanced Synthesis and Catalysis, Wiley-VCH Verlag, 2019, 361 (9), pp.2025-2030. ⟨10.1002/adsc.201801526⟩. ⟨hal-02093077⟩

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