Bridge heteroarylation of bicyclo[1.1.1]pentane derivatives

Anderson, Joseph M. and Measom, Nicholas D. and Murphy, John A. and Poole, Darren L. (2023) Bridge heteroarylation of bicyclo[1.1.1]pentane derivatives. Organic Letters, 25 (12). 2053–2057. ISSN 1523-7060 (https://doi.org/10.1021/acs.orglett.3c00412)

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Abstract

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

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