Cyclopropanation through Photoredox Catalysis

  • Author: Charlotte Gers-Panther
  • Published Date: 23 February 2017
  • Source / Publisher: European Journal of Organic Chemistry/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
thumbnail image: Cyclopropanation through Photoredox Catalysis

Related Societies

Cyclopropane rings can be found in a large variety of secondary metabolites with diverse biological activities. This has contributed to their importance in medicinal and agricultural chemistry. The synthesis of cyclopropanes can be achieved by using different catalytic processes involving iodomethylzinc carbenoids, diazomethane, and sulfur or nitrogen ylides. Interestingly, methods based on radical species are still scarce.

Ana M. del Hoyo and Marcos García Suero, Institute of Chemical Research of Catalonia (ICIQ), Tarragona, Spain, have developed a cyclopropanation reaction of Michael-acceptor compounds. The reaction uses diiodomethane as a methylene-transfer reagent and the Ru-based photoredox catalyst [Ru(bpy)3](PF6)2 (bpy = 2,2’-bipyridine). The reaction proceeds via an iodomethyl radical carbenoid, which is generated photocatalytically and subsequently cyclopropanates the alkene group of Michael-acceptor compounds.

The reaction tolerates a large variety of differently substituted chalcones and heteroaryl analogues. α,β-Unsaturated aldehydes or methyl ketones are also converted. Interestingly, 1,1-diodoethane can also be used as a methylene source in a selective manner.


Article Views: 3725

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

If you would like to reuse any content, in print or online, from, please contact us first for permission and consult our permission guidance prior to making your request

Follow on Facebook Follow on Twitter Follow on YouTube Follow on LinkedIn Follow on Instagram RSS Sign up for newsletters

Magazine of Chemistry Europe (16 European Chemical Societies) published by Wiley-VCH