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. 2024 Jan 8;63(2):e202316064.
doi: 10.1002/anie.202316064. Epub 2023 Dec 8.

Vitamin B12 -Photocatalyzed Cyclopropanation of Electron-Deficient Alkenes Using Dichloromethane as the Methylene Source

John Hayford G Teye-Kau  1 , Mayokun J Ayodele  2 , Spencer P Pitre  1
Affiliations

Vitamin B12 -Photocatalyzed Cyclopropanation of Electron-Deficient Alkenes Using Dichloromethane as the Methylene Source

John Hayford G Teye-Kau et al. Angew Chem Int Ed Engl. .

Abstract

The cyclopropyl group is of great importance in medicinal chemistry, as it can be leveraged to influence a range of pharmaceutical properties in drug molecules. This report describes a Vitamin B12 -photocatalyzed approach for the cyclopropanation of electron-deficient alkenes using dichloromethane (CH2 Cl2 ) as the methylene source. The reaction proceeds in good to excellent yields under mild conditions, has excellent functional group compatibility, and is highly chemoselective. The scope could also be extended to the preparation of D2 -cyclopropyl and methyl-substituted cyclopropyl adducts starting from CD2 Cl2 and 1,1-dichloroethane, respectively.

Keywords: Cobalt; Cyclopropanation; Photocatalysis; Radicals; Visible Light.

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