Regiocontrolled Annulation of Benzocyclobutenols with Alkynes.

Abstract

A tandem reaction that involves an unprecedented Rh-catalyzed intramolecular annulation of benzocyclobutenols with alkynes and subsequent ZnCl2-promoted dehydration was developed, offering an efficient approach to 2H-furan-, pyran-, and oxepine-fused naphthalenes. Furthermore, the 2H-furan motif may undergo a ring-opening reaction through Fe-catalyzed reductive C-O bond cleavage. As a consequence, the formal intermolecular annulation of 2-hydroxybenzocyclobutenols with alkynes was realized with complete regioselectivity through a two-step protocol.

• Authors: Qin-Qiong Zeng, Yong-Qi Wang, Lang Cheng, Bi-Qin Wang, Ping Hu, Feijie Song
• Journal: Organic letters (Org Lett) Vol. 24 Issue 16 Pg. 3058-3063 (Apr 29 2022) ISSN: 1523-7052 [Electronic] United States
• PMID: 35426691 (Publication Type: Journal Article)