Nickel-Catalyzed Electro-Reductive Cross-Coupling of Aliphatic N-Acyl Imides with Alkyl Halides as a Strategy for Dialkyl Ketone Synthesis: Scope and Mechanistic Investigations was written by Kerackian, Taline;Bouyssi, Didier;Pilet, Guillaume;Medebielle, Maurice;Monteiro, Nuno;Vantourout, Julien C.;Amgoune, Abderrahmane. And the article was included in ACS Catalysis in 2022.Electric Literature of C9H11BrO This article mentions the following:
The development and in-depth study of a cross-electrophile coupling of alkyl N-acyl imides with alkyl halides relying on the combination of nickel catalysis and electrochem. are described. This methodol. takes advantages of the stability and simple access of N-acyl imides as coupling partners for the selective synthesis of dissym. dialkyl ketones. Noteworthy, the developed electrochem. protocol affords selective access to linear alkyl ketones when using primary alkyl bromides featuring different chain lengths. Mechanistic studies including cyclic voltammetry, stoichiometric reactions, and isolation of catalytic intermediates provide a set of fundamental insights into monovalent (bpy)nickel-mediated activation of alkyl halides and alkyl N-acyl imides. Alkyl bromides react with electrogenerated (bpy)Ni(I) species via single-electron oxidation to give alkyl radicals. N-Acyl imides are shown to undergo spontaneous C-N bond oxidative addition at both (bpy)Ni(0) and (bpy)Ni(I) species, leading to Ni(II) acyl intermediates. A stable nickel(II) acyl complex has also been isolated and fully characterized, and its catalytic competency is demonstrated. Finally, electrogenerated (bpy)Ni(I)-acyl species are shown to react with both alkyl bromide and alkyl N-acyl imides. Overall, these investigations allowed for a comprehensive mechanistic picture of this selective cross-electrophile coupling to be assembled. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Electric Literature of C9H11BrO).
1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Electric Literature of C9H11BrO
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary