Dearomative Cyclopropanation of Naphthols via Cyclopropene Ring‐Opening. (10th January 2022)

• Record Type: Journal Article
• Authors: Baker, Rachel J.; Ching, Justin; Hou, Teh Ren; Franzoni, Ivan; Lautens, Mark
• Is Part Of: Angewandte Chemie. Volume 134:Number 8(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-01-10
• Subjects: Cyclopropanation -- Cyclopropenes -- Dearomative -- Naphthols -- Rhodium catalysis; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202116171
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: The dearomatization of 2‐naphthols represents a simple method for the construction of complex 3D structures from simple planar starting materials. We describe a cyclopropanation of 2‐naphthols that proceeds via cyclopropene ring‐opening using rhodium and acid catalysis under mild conditions. The vinyl cyclopropane molecules were formed with high chemoselectivity and scalability, which could be further functionalized at different sites. Both computational and experimental evidence were used to elucidate the reaction mechanism. Abstract : The rhodium‐ and acid‐catalyzed dearomative cyclopropanation of naphthols from cyclopropene ring‐opening has been described. The reaction is scalable and highly chemoselective, and the vinyl cyclopropane products can be uniquely diversified. Experimental and computational studies support the proposed mechanism.