Ring-Opening Cross-Coupling of Cyclopropanols with Electrophilic Alkenes via Photoinduced Charge Transfer Facilitated by Decatungstate Catalyst

31 July 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


A unique property of aryl-substituted tertiary cyclopropanols to form photoactive electron donor-acceptor (EDA) complexes with electron-deficient olefins has been applied for the synthesis of distantly functionalized ketones via redox-neutral addition of cyclopropanol-derived β-ketoalkyl radicals to the electrophilic double bond of the olefins. The reaction occurs upon UV light irradiation that triggers homolytic cleavage of the cyclopropane ring through photoinduced charge transfer in the formed EDA complexes. The reaction rate drastically increases in the presence of tetrabutylammonium decatungstate (TBADT), which facilitates the electron transfer between the reactants and allows the reaction to occur even in the case of cyclopropanols that cannot form EDA complexes. The described transformations proceed under mild conditions and do not require stoichiometric oxidants. The generality and robustness of the developed method have been validated on a broad scope of cyclopropanol and alkene substrates, delivering the corresponding adducts in up to 92% yield. Successful scale up under continuous flow conditions has also been demonstrated.


electron donor-acceptor complex
single electron transfer
flow chemistry

Supplementary materials

Supporting Information
The Supporting Information contains general information, experimental setups, optimization and mechanistic studies, general procedures, compounds characterization data and NMR spectra.


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