Redox‐Neutral Dual Functionalization of Electron‐Deficient Alkenes

• Published in: Chemistry : a European journal Vol. 23; no. 31; pp. 7444 - 7447
• Main Authors: Pettersson, Fredrik, Bergonzini, Giulia, Cassani, Carlo, Wallentin, Carl‐Johan
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 01.06.2017; Wiley Subscription Services, Inc; John Wiley and Sons Inc
• Subjects: acyl radicals; Alkenes; Biochemistry and Molecular Biology; Biokemi och molekylärbiologi; Carboxylic acids; Cascade chemical reactions; cascade transformation; Catalysis; Chemistry; Chemistry, Multidisciplinary; Communication; Communications; Diketones; multicomponent reactions; Photoredox catalysis; Physical Sciences; Science & Technology; Single electrons; Substrates; multicomponent reactions; STYRENES; PHOTOCATALYSIS; CASCADE; VISIBLE-LIGHT; KETONES; acyl radicals; cascade transformation; carboxylic acids; COMPLEXITY; LIGHT PHOTOREDOX CATALYSIS; photoredox catalysis; METAL-FREE; CARBOXYLIC-ACIDS
• ISSN: 0947-6539; 1521-3765; 1521-3765
• DOI: 10.1002/chem.201701589

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.