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. 2023 Sep 4;62(36):e202308379.
doi: 10.1002/anie.202308379. Epub 2023 Jul 27.

Late-Stage Aryl C-H Bond Cyclopropenylation with Cyclopropenium Cations

Hang-Fei Tu  1 , Aliénor Jeandin  1   2 , Corentin Bon  3 , Cara Brocklehurst  3 , Fabio Lima  3 , Marcos G Suero  1
Affiliations

Late-Stage Aryl C-H Bond Cyclopropenylation with Cyclopropenium Cations

Hang-Fei Tu et al. Angew Chem Int Ed Engl. .

Abstract

Herein, we disclose the first regio-, site- and chemoselective late-stage (hetero)aryl C-H bond cyclopropenylation with cyclopropenium cations (CPCs). The process is fast, operationally simple and shows an excellent functional group tolerance in densely-functionalized drug molecules, natural products, agrochemicals and fluorescent dyes. Moreover, we discovered that the installation of the cyclopropene ring in drug molecules could not only be used to shield against metabolic instability but also as a synthetic tool to reach medicinally-relevant sp3 -rich scaffolds exploiting the highly-strained nature of the cyclopropene ring with known transformations.

Keywords: Cyclopropenes; Cyclopropenium Cations; Drug Discovery; Late-Stage C−H Functionalization; Metabolic Stability.

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