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)

1 ISM - Institut des Sciences Moléculaires
2 IPREM - Institut des sciences analytiques et de physico-chimie pour l'environnement et les materiaux

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

Domains: Chemical Sciences; Theoretical and/or physical chemistry; Chemical Sciences; Analytical chemistry; Chemical Sciences; Polymers; Chemical Sciences; Material chemistry

Julien Gicquiaud, Antoine Hacihasanoğlu, Philippe Hermange, Jean-Marc Sotiropoulos, Patrick Y. Toullec. Brønsted Acid‐Catalyzed Carbocyclization of 2‐Alkynyl Biaryls. Advanced Synthesis and Catalysis, 2019, 361 (9), pp.2025-2030. ⟨10.1002/adsc.201801526⟩. ⟨hal-02093077⟩