2012
DOI: 10.1002/anie.201200859
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N,N‐Dimethylformamide: A Multipurpose Building Block

Abstract: Often used as a common solvent for chemical reations and utilized widely in industry as a reagent, N,N-dimethylformamide (DMF) has played an important role in organic synthesis for a long time. Numerous highly useful articles and reviews discussing its utilizations have been published. With a focus on the performance of DMF as a multipurpose precursor for various units in numerous reactions, this Minireview summarizes recent developments in the employment of DMF in the fields of formylation, aminocarbonylation… Show more

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Cited by 387 publications
(167 citation statements)
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References 122 publications
(45 reference statements)
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“…The relative strong acidity of carboxylic functions in pyromellitic acid is not favorable for complexation of the ura-nium cation in DMF. Then, a small amount of water could favor the hydrolysis of DMF [35,36] under solvothermal conditions, [37][38][39][40] and the production of dimethylamine, [41] which is required to fully deprotonate pyromellitic acid. Such a reaction is not required with carboxylic acids with lower pK a values, since dimethylamine produced by thermal decomposition of DMF is sufficient to generate the reactive carboxylate function.…”
Section: Discussionmentioning
confidence: 99%
“…The relative strong acidity of carboxylic functions in pyromellitic acid is not favorable for complexation of the ura-nium cation in DMF. Then, a small amount of water could favor the hydrolysis of DMF [35,36] under solvothermal conditions, [37][38][39][40] and the production of dimethylamine, [41] which is required to fully deprotonate pyromellitic acid. Such a reaction is not required with carboxylic acids with lower pK a values, since dimethylamine produced by thermal decomposition of DMF is sufficient to generate the reactive carboxylate function.…”
Section: Discussionmentioning
confidence: 99%
“…It is worth to illustrate that the introduction of the NMe2 functionality by SNAr substitution, occurred unexpectedly from DMF decomposition. Indeed, some literature reports 47,48 described that under specific reaction conditions DMF could decompose providing a source of-NMe2 group, which in our case would be the responsible of the second substitution on the naphthalene core.…”
Section: Computational Detailsmentioning
confidence: 71%
“…A mixture of compound 1 (0.912g, 2mmol) and 4-dimethylaminopyridine (DMAP 0.012g, 0.1mmol) was taken in 20 ml of N, N-dimethylformamide (DMF) 37,38 . The resulting solution was heated at reflux and stirred for 8 hours.…”
Section: Synthesis Of Compound Lmentioning
confidence: 99%