Oxidative cleavage of alkenes by photosensitized nitroarenes

Patra, Tuhin and Wirth, Thomas ORCID: https://orcid.org/0000-0002-8990-0667 2022. Oxidative cleavage of alkenes by photosensitized nitroarenes. Angewandte Chemie International Edition 61 (47) , e202213772. 10.1002/anie.202213772

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Abstract

Oxidative cleavage of alkenes into carbonyl molecules mainly relies on either ozonolysis or Lemieux-Johnson oxidation involving high valent transition metal oxides. Safety, technical concerns and highly oxidizing conditions of both these procedures limited their adoption in streamlined synthesis. Like ozone, photosensitized nitroarenes can deliver similar types of [3+2] cycloaddition products with alkenes through biradical formation and the resulting “N-doped” ozonides can safely be converted to the corresponding carbonyl compounds through hydrolysis. The high prevalence of nitroarenes with diverse electronic and steric profiles combined with the mild oxidizing power allow to modulate site-selectivity and tolerate highly sensitive functional groups ideal for application in complex molecular setup.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Publisher:	Wiley
ISSN:	1433-7851
Funders:	BAE Systems, Falcon and the Welsh Government (SMART Expertise grant).
Date of First Compliant Deposit:	10 November 2022
Date of Acceptance:	7 October 2022
Last Modified:	07 Oct 2023 21:31
URI:	https://orca.cardiff.ac.uk/id/eprint/154095

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