Recent Uses of N,N-Dimethylformamide and N,N-Dimethylacetamide as Reagents

Abstract

N,N-Dimethylformamide and N,N-dimethylacetamide are multipurpose reagents which deliver their own H, C, N and O atoms for the synthesis of a variety of compounds under a number of different experimental conditions. The review mainly highlights the corresponding literature published over the last years.

The Reims Journey Towards Discovery and Understanding of Pd-Catalyzed Oxidations

“…Our interest in the Pd-catalyzed oxidations and in the synthetic properties of DMF [91][92][93] and BQ [94] urged us to investigate the Wacker reaction of terminal alkenes 33 with ESI-MS, using BQ as the terminal oxidant (Equation (20)) [95]. The report of Jacobs' team about the phenol-mediated epoxidation of alkenes by H2O2 under metal-free conditions [81] led us to propose in 2005 the mechanism depicted in Scheme 11 [80].…”

“…Our interest in the Pd-catalyzed oxidations and in the synthetic properties of DMF [91][92][93] and BQ [94] urged us to investigate the Wacker reaction of terminal alkenes 33 with ESI-MS, using BQ as the terminal oxidant (Equation (20)) [95]. (19) Recycling of the Pd(OCOCF 3 ) 2 /L H catalytic system led to gradual loss of activity, the 4th reuse in H 2 O/MeOH yielding 35% and 24% of 30 and 31 Me , respectively, from 29 [85].…”

“…Our interest in the Pd-catalyzed oxidations and in the synthetic properties of DMF [91][92][93] and BQ [94] urged us to investigate the Wacker reaction of terminal alkenes 33 with ESI-MS, using BQ as the terminal oxidant (Equation (20)) [95].…”

Photocatalyzed Chemo‐Selective Alkylation of Quinones and Phenothiazinones with Alkyl Amides: Photophysical and Cytotoxic Activity Studies

“…One of the most significant challenges in synthetic chemistry is chemoselective functionalisation of molecules possessing multiple functional groups [9e–g] . Appealingly, the popular polar solvents N,N ‐dimethylacetamide (DMA, 2 b ) N, N ‐dimethylformamide (DMF, 2 d ) and other alkyl amides consists of several functional groups such as 2 amides (−NH), amidoalkyl (−NH(C=O)CH 3 ), dialkylamine (N(Me) 2 ), amido carbonyl (−NH(C=O)CH 3 ) and can be used as versatile synthon in organic transformations – [10a–] . Although, N ‐methylacetamide (NMA, 2 a ) was N−H functionalised to form C−N bond, [11a–d] there is no report on selective functionalization of its N −CH 3 group.…”

Eco-Friendly Syntheses of 2-Substituted Benzoxazoles and 2-Substituted Benzothiazoles from 2-Aminophenols, 2-Aminothiophenols and DMF Derivatives in the Presence of Imidazolium Chloride

“…We have recently reported [27,28] the use of imidazolium chloride as catalyst and DMF derivatives as eco-friendly carbon sources in the formation of amido bonds and benzimidazole derivatives (Scheme 2). We envisioned that this process might be extended to 2-aminophenols and 2-aminothiophenols, which would provide access to benzoxazole and benzothiazole derivatives using inexpensive, stable, and easy to synthesize DMF derivatives as carbon sources and imidazolium chloride as the promoter [29,30,31].…”