N,N‐Dimethylformamid: ein vielseitiger Baustein für die Synthese

Abstract

Die organische Synthese profitiert seit langem von N,N‐Dimethylformamid (DMF), das als Lösungsmittel für chemische Reaktionen und industriell auch als Reagens breit eingesetzt wird. Zu diesen Anwendungen sind bereits zahlreiche hilfreiche Artikel und Übersichten erschienen. Dieser Kurzaufsatz fasst die Verwendung von DMF als Allzweckvorstufe zusammen und stellt die neuen Entwicklungen bei Formylierungen, Aminocarbonylierungen, Aminierungen, Amidierungen, Cyanierungen und in der Reaktion mit Arinen vor.

Lewis Acid‐Catalyzed Reductive Amination of Aldehydes and Ketones with N,N‐Dimethylformamide as Dimethylamino Source, Reductant and Solvent

“…On the other hand, N , N ‐dimethylformamide (DMF) is an excellent polar solvent wildly used in almost all laboratories. More importantly, DMF can act as reactant to incorporate CO, HCO, Me 2 N, Me 2 NCO and “C” (to form CN) units into products ,. Besides, DMF has also been reported to be an effective ligand for various metals, such as Cu(II), Ag(I), Au(III) and Pd(II), and DMF was able to further reduce these metal complexes under suitable conditions ,.…”

Oxidative C–Se Coupling of Formamides and Diselenides by Using Aqueous tert‐But­yl Hydroperoxide: A Convenient Synthesis of Selenocarbamates

“…Dimethylformamide is normally used as a solvent,13 but is also considered as a source of CO, Me 2 N, Me 2 NCO and oxygen 14. However, the direct C–H activation of formamides has also been reported 15–18.…”

Highly Efficient Ruthenium‐Catalyzed N‐Formylation of Amines with H2 and CO2

“…[1] Fore xample, N,N-dimethylformamide (DMF), an industrial solvent with huge annual global market volume, has also served as an extremely versatile multipurpose reagent in numerous synthetic processes. [2] Among the methods developed for the production of various formamides, the most general approach is the N-formylation of amines with formic acid or formate in the presence of ac atalyst. [3] Industrially,D MF is produced by aN aOCH 3 -catalyzed reaction of dimethylamine with toxic CO in methanol.…”