N,N-Dimethylformamide: much more than a solvent

Мuzart, Jacques

doi:10.1016/j.tet.2009.06.091

Cited by 389 publications

(177 citation statements)

References 124 publications

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“…We concluded that small amounts of water in reagent grade DMF (entry 7) may lead to in situ MIDA ester cleavage due to possible (basic) dimethylamine generation. 28 The result employing acetonitrile (entry 1), although comparable to that of Entry 6, was deemed to be the most promising, due to the reduced toxicity and lower boiling point of this solvent. 29,30 Interestingly, the use of molecular sieves (entry 2) did not push the reaction to completion.…”

Section: Introductionmentioning

confidence: 96%

Microwave-mediated synthesis of N-methyliminodiacetic acid (MIDA) boronates

Kemmitt

Emmerson

et al. 2014

Tetrahedron

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(2014) Microwavemediated synthesis of N-methyliminodiacetic acid (MIDA) boronates. Tetrahedron, 70 (47). pp. [9125][9126][9127][9128][9129][9130][9131] This version is available from Sussex Research Online: http://sro.sussex.ac.uk/53847/ This document is made available in accordance with publisher policies and may differ from the published version or from the version of record. If you wish to cite this item you are advised to consult the publisher's version. Please see the URL above for details on accessing the published version. Copyright and reuse:Sussex Research Online is a digital repository of the research output of the University.Copyright and all moral rights to the version of the paper presented here belong to the individual author(s) and/or other copyright owners. To the extent reasonable and practicable, the material made available in SRO has been checked for eligibility before being made available.Copies of full text items generally can be reproduced, displayed or performed and given to third parties in any format or medium for personal research or study, educational, or not-for-profit purposes without prior permission or charge, provided that the authors, title and full bibliographic details are credited, a hyperlink and/or URL is given for the original metadata page and the content is not changed in any way. ABSTRACT: A library of over twenty, mainly aryl or heteroaryl, N-methyliminodiacetic acid (MIDA) boronates has been synthesized. A rapid microwave-mediated (MW) method (5-10 mins) has been developed using polyethylene glycol 300 (PEG 300) as solvent. However, acetonitrile (MeCN) and dimethylformamide (DMF) were found to be alternative solvents, the latter especially for 2-substituted aryl boronic acids.

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Section: Introductionmentioning

confidence: 96%

Microwave-mediated synthesis of N-methyliminodiacetic acid (MIDA) boronates

Kemmitt

Emmerson

et al. 2014

Tetrahedron

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“…All 1 H NMR spectra were identical, presenting well-characterized signals in the aliphatic area and a sharp singlet around 8.00 ppm, without any characteristic signals for aromatic protons. At that point we realized our mistake, DMF being known to be ''much more than a solvent'', as pointed out by Muzart [8] and namely known as a slow formylation reagent for both aromatic and aliphatic amines [9]. Therefore, the natural conclusion was that a reaction indeed took place and that the reagents in that process were HMDA and DMF, without any participation of the less reactive ketones.…”

Section: Resultsmentioning

confidence: 99%

Serendipitous synthesis of a cyclic formamidine. Application to the synthesis of polyazamacrocycles

Simion

Gherase

Sima

et al. 2015

Comptes Rendus. Chimie

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“…With this modulated glycosylation method, DMF is employed to entrap the cationic glycosyl oxacarbenium ion as a glycosl imidate. [19,20] Further reaction of the imidate with an acceptor produces the desired cis a-glycoside in high selectivity. Because the modulation method includes a pre-activation step, it is further elaborated to iterative glycosylation for thioglycosyl substrates.…”

Section: Introductionmentioning

confidence: 99%

Iterative One‐Pot α‐Glycosylation Strategy: Application to Oligosaccharide Synthesis

Liu¹,

Mulani²,

Mong³

2012

Adv Synth Catal

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Based on the combined use of dimethyl-A C H T U N G T R E N N U N G formamide (DMF) modulation and neighboring group participation, three iterative one-pot a-glycosylation methods, i.e., one-pot (a,a)-, one-pot (b,a)-, and one-pot (a,b)-glycosylations, were developed. These methods are applicable to a range of thioglycosyl donors, confer stereocontrol in a-/b-glycosidic bond formation, and thus provide for rapid access to oligosaccharides with various permutations of anomeric configurations. The utility of these one-pot glycosylation methods is demonstrated in the synthesis of eight non-natural and natural oligosaccharide targets, including the core 1 serine conjugate, core 8

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N,N-Dimethylformamide: much more than a solvent

Cited by 389 publications

References 124 publications

Microwave-mediated synthesis of N-methyliminodiacetic acid (MIDA) boronates

Microwave-mediated synthesis of N-methyliminodiacetic acid (MIDA) boronates

Serendipitous synthesis of a cyclic formamidine. Application to the synthesis of polyazamacrocycles

Iterative One‐Pot α‐Glycosylation Strategy: Application to Oligosaccharide Synthesis

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