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Updated: Aug 6, 2025

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Bridge Heteroarylation of Bicyclo[1.1.1]pentane Derivatives
Joseph M Anderson1,2, Nicholas D Measom1, John A Murphy2
1Medicinal Chemistry, GSK Medicines Research Centre, Gunnels Wood Road, Stevenage SG1 2NY, U.K.
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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