Brønsted Acid‐Catalyzed Carbocyclization of 2‐Alkynyl Biaryls

Julien Gicquiaud; Antoine Hacıhasanoğlu; Philippe Hermange; Jean-Marc Sotiropoulos; Patrick Toullec

doi:10.1002/adsc.201801526

Journal articles

Brønsted Acid‐Catalyzed Carbocyclization of 2‐Alkynyl Biaryls

Julien Gicquiaud ¹ Antoine Hacıhasanoğlu ¹ Philippe Hermange ¹ Jean-Marc Sotiropoulos ² Patrick 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

Domain :

Chemical Sciences / Theoretical and/or physical chemistry

Chemical Sciences / Analytical chemistry

Chemical Sciences / Polymers

Chemical Sciences / Material chemistry

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https://hal-univ-pau.archives-ouvertes.fr/hal-02093077
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Submitted on : Monday, April 8, 2019 - 4:14:41 PM
Last modification on : Thursday, March 5, 2020 - 7:17:39 PM

Brønsted Acid‐Catalyzed Carbocyclization of 2‐Alkynyl Biaryls

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