![Author ORCID: We display the ORCID iD icon alongside authors names on our website to acknowledge that the ORCiD has been authenticated when entered by the user. To view the users ORCiD record click the icon. [opens in a new tab]](https://chemrxiv.org/engage/assets/public/chemrxiv/images/logos/orcid.png)
Abstract
A protocol for the oxidation of alkenes to carbonyls and acetonides via the interplay of photoexcited nitroarenes and Lewis acid catalysis is described. Terminal 1,1-disubstitued alkenes were oxidized selectively to the aldehyde products, while tri- and tetrasubstituted alkenes generated ketone products with anti-Markovnikov selectivity. Terminal mono-substituted alkenes were oxidized to acetonides when acetone was employed as a co-solvent. The mild conditions of the reaction allow for a wide range of alkenes to be oxidized. Mechanistic studies support that Lewis acid coordination to the 1,3,2-dioxazolidine intermediate formed by irradiation of the nitroarene and alkene results in a Meinwald-like rearrangement to generate carbonyl derivatives. In the presence of acetone, acetonides are formed from the same intermediate through a nucleophilic substitution pathway.
Supplementary materials
Title
Supporting Information
Description
Experimental details, optimization studies, characterization data, and NMR spectra (PDF).
Actions
