Bridge Heteroarylation of Bicyclo[1.1.1]pentane Derivatives

• DOI: 10.1021/acs.orglett.3c00412
• Publication Date: 2023-03-17T13:18:41Z
• Authors: Joseph M. Anderson; Nicholas D. Measom; John A. Murphy; Darren L. Poole
• Keywords: Pentane; Bridge (graph theory); Hexane

Herein, we report the decarboxylative Minisci heteroarylation of bicyclo[1.1.1]pentane (BCP) and 2-oxabicyclo[2.1.1]hexane (oBCH) derivatives at bridge positions. In an operationally simple, photocatalyst-free process, free carboxylic acids are directly coupled with nonprefunctionalized heteroarenes to provide rare examples polysubstituted BCP oBCH in synthetically useful yields. Additionally, impact core on physicochemical properties a representative example compared those its all-aromatic ortho- meta-substituted analogues is evaluated.