Photocatalyst-free hydroacylations of electron-poor alkenes and enones under visible-light irradiation

• Published in: Organic & biomolecular chemistry Vol. 2; no. 36; pp. 7245 - 7249
• Main Authors: Pálvölgyi, Ádám Márk, Ehrschwendtner, Florian, Schnürch, Michael, Bica-Schröder, Katharina
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 21.09.2022; Royal Society of Chemistry; The Royal Society of Chemistry
• Subjects: Alkenes; Alkenes - chemistry; Catalysis; Chemistry; Chemistry, Organic; Electrons; Esters; Free radicals; Free Radicals - chemistry; Irradiation; Light irradiation; Photocatalysts; Photochemical Processes; Physical Sciences; Quinones; Science & Technology; Substrates; HANTZSCH ESTERS; QUINONE METHIDES
• ISSN: 1477-0520; 1477-0539; 1477-0539
• DOI: 10.1039/d2ob01364a

Herein we present a photocatalyst- and additive-free radical hydroacylation of electron-poor double bonds under mild reaction conditions. Using 4-acyl-Hantzsch ester radical reservoirs, various Michael acceptors, enones and para -quinone methide substrates could be used. The protocol enabled further derivatizations and it could also be extended to a few unactivated alkenes. Moreover, the nature of the radical process was also investigated. 4-Acyl-Hantzsch esters have been used for the radical hydroacylation of various alkene acceptors. This protocol provided high yields for three different substrate classes and neither a photocatalyst nor additives were required.