Enantiospecific Generation and Trapping Reactions of Aryne Atropisomers

Yun-Long Wei (1) , Guillaume Dauvergne (1) , Jean Rodriguez (1) , Yoann Coquerel (1)

1 ISM2 - Institut des Sciences Moléculaires de Marseille

Enantioenriched aryne atropisomers having a biaryl stereogenic axis vicinal to the reactive triple bond are demonstrated to exist. These reaction intermediates are easily produced in situ and can undergo the standard aryne cycloaddition chemistry in an enantiospecific manner. Notably, the aryne atropisomers herein have allowed the practical syntheses of a small nanographene as well as some triptycene and anthracene derivatives that embed stereogenic axes of controlled absolute configurations.

Keywords: biaryl; aryne; atropisomer; nanographene

Domains: Organic chemistry

Yun-Long Wei, Guillaume Dauvergne, Jean Rodriguez, Yoann Coquerel. Enantiospecific Generation and Trapping Reactions of Aryne Atropisomers. Journal of the American Chemical Society, 2020, 142 (40), pp.16921-16925. ⟨10.1021/jacs.0c08218⟩. ⟨hal-02990635⟩