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

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 (C...

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Veröffentlicht in:Angewandte Chemie International Edition 2024-01, Vol.63 (2), p.e202316064-n/a
Hauptverfasser: Teye‐Kau, John Hayford G., Ayodele, Mayokun J., Pitre, Spencer P.
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Ayodele, Mayokun J.
Pitre, Spencer P.
description 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 (CH2Cl2) 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 CD2Cl2 and 1,1‐dichloroethane, respectively. We report a vitamin B12‐photocatalyzed strategy for the cyclopropanation of electron‐deficient alkenes using dichloromethane (CH2Cl2) as the methylene source. The reaction has excellent functional group tolerance, is highly chemoselective, and the scope can be extended to other 1,1‐dichloroalkanes for the preparation of D2‐cyclopropyl and methyl‐substituted cyclopropyl adducts, all of which are important isosteres in medical chemistry.
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source Wiley Online Library Journals Frontfile Complete
subjects Adducts
Alkenes
Cobalt
Cyanocobalamin
Cyclopropanation
Dichloroethane
Dichloromethane
Functional groups
Organic compounds
Photocatalysis
Radicals
Visible Light
Vitamin B12
title Vitamin B12‐Photocatalyzed Cyclopropanation of Electron‐Deficient Alkenes Using Dichloromethane as the Methylene Source
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