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Visible light mediated synthesis of β chloro ketones from aryl cyclopropanes
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.ORCID iD: 0000-0003-4646-0216
2019 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 58, p. 8577-8580Article in journal (Refereed) Published
Abstract [en]

We report the visible light mediated synthesis of β chloro ketones from aryl cyclopropanes, oxygen, hydrochloric acid and nitric acid. The operationally simple and catalyst free method uses cheap standard lab reagents and displays a broad functional group tolerance. Moreover, scale up of the reaction and late stage functionalization of bioactive compounds is possible, providing the opportunity to utilize the cyclopropane ring as a masked β chloro ketone in a reaction sequence. We propose a light‐driven radical chain reaction initiated by the reaction of diluted hydrochloric and nitric acid producing small quantities of molecular chlorine. The mechanistic hypothesis is supported by 18O labelling and UV‐VIS experiments, cyclovoltammetry and several control reactions.

Place, publisher, year, edition, pages
Wiley Online Library , 2019. Vol. 58, p. 8577-8580
Keywords [en]
photochemistry, aryl cyclopropane, β chloro ketone, radical chain reaction, late-stage modification
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:umu:diva-157629DOI: 10.1002/anie.201902473ISI: 000476608700052PubMedID: 30901148OAI: oai:DiVA.org:umu-157629DiVA, id: diva2:1299223
Available from: 2019-03-26 Created: 2019-03-26 Last updated: 2019-08-14Bibliographically approved

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Singh, PardeepAlmqvist, Fredrik

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