3 years ago

Redox-Neutral Dual Functionalization of Electron-Deficient Alkenes

Redox-Neutral Dual Functionalization of Electron-Deficient Alkenes
Giulia Bergonzini, Carlo Cassani, Carl-Johan Wallentin, Fredrik Pettersson
Visible-light photoredox catalysis has been utilized in a new multicomponent reaction forming β-functionalized δ-diketones under mild conditions in an operationally convenient manner. Single-electron reduction of in situ generated carboxylic acid derivatives forms acyl radicals that react further via 1,2-acylalkylation of olefins in an intermolecular, three-components cascade reaction, giving valuable synthetic entities from readily available starting materials. A diverse set of substrates has been used, demonstrating robust methodology with broad substrate scope. Photoredox catalysis: Acyl radicals have been accessed from simple aromatic carboxylic acids under visible-light photoredox catalysis. The method offers an atom-efficient entry to valuable synthetic entities from readily available starting materials without the need of high-energy UV irradiation, stoichiometric oxidants, high CO pressure, or high temperature.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201701589

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