Novel One-Pot Vicinal Double C-Acylation of Styrenes and Methacrylates by Electroreduction

Abstract

[reaction: see text] Electroreduction of styrenes or alkyl methacrylates in the presence of aliphatic acid anhydrides or N-acylimidazoles with an undivided cell equipped with zinc electrodes as the anode and the cathode brought about novel one-pot vicinal double C-acylation to afford the corresponding 1,4-diketones in satisfactory yields.

Contributions of organic electrosynthesis to green chemistry

“…The electroreduction of styrenes or alkyl methacrylates in the presence of aliphatic acid anhydrides or Nacylimidazoles in an undivided cell with zinc electrodes afforded in a twofold carbon-acylation 1,4-diketones in 33-85% yield [52].…”

1,4-Bis(4-chlorophenyl)butane-1,4-dione

“…For applications of the title compound, see: Rao et al (2004); Stauffer & Neier (2000); Shridhar et al (1982). For the preparation of the title compound, see: Stetter (1976); Nimgirawath et al (1976); Yamamoto et al (2003); Yuguchi et al (2004).…”

Intermolecular Stetter Reactions on Morita‐Baylis‐Hillman Adducts: an Approach to Highly Functionalized 1,4‐Dicarbonyl Compounds

“…For example, the nucleophilic substitution of α ‐haloketones by enolates is a robust method to access 1,4‐diketone compounds . Other alternative methods that are often employed, include conjugate addition of enolates to Michael acceptors, oxidative coupling of enolates, organo‐cobalt and organo‐samarium additions, homologation reactions of 1,3‐dicarbonyl compounds and the C ‐acylation of styrenes . Stetter reactions between aldehydes and Michael acceptors catalyzed by N‐ heterocyclic carbenes (NHC's) present a powerful approach to access 1,4‐dicarbonyls .…”

“…[15][16][17][18] Other alternative methods that are often employed, include conjugate addition of enolates to Michael acceptors, [19][20][21] oxidative coupling of enolates, [22,23] organo-cobalt and organo-samarium additions, [24][25][26] homologation reactions of 1,3-dicarbonyl compounds [27][28][29][30] and the Cacylation of styrenes. [31,32] Stetter reactions between aldehydes and Michael acceptors catalyzed by N-heterocyclic carbenes (NHC's) present a powerful approach to access 1,4-dicarbonyls. [33][34][35][36][37][38] Notwithstanding the variety of methods, improvements are still necessary to achieve improvements in terms of substrate scope, mild reaction conditions, environmentally safe reagents, and commercially available starting materials.…”