Selective <i>N</i>‐Alkylation of Arylamines with Alkyl Chloride in Ionic Liquids: Scope and Applications

Monopoli, Antonio; Cotugno, Pietro; Cortese, Marina; Calvano, Cosima Damiana; Ciminale, Francesco; Nacci, Angelo

doi:10.1002/ejoc.201200202

Cited by 34 publications

(13 citation statements)

References 85 publications

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“…However, despite the number of protocols devoted to the oxidative homocondensation of amines, carrying out these reactions in environmentally friendly solvents remains unexplored, and, to the best of our knowledge, no examples of successful methods performed in ionic liquids (ILs)14 have been reported until now. Continuing our interest in the use of ILs in organic synthesis,15 we recently found that the N ‐alkylation of arylamines with alkyl chlorides can be performed in high yields and with high selectivities in molten tetraalkylammonium salts at 100 °C 15d. However, this reaction is not applicable to benzylamines, since appreciable amounts of the corresponding homocondensed imines were detected in addition to the alkylation product.…”

Section: Introductionmentioning

confidence: 99%

Ionic‐Liquid‐Assisted Metal‐Free Oxidative Coupling of Amines To Give Imines

Monopoli¹,

Cotugno²,

Iannone³

et al. 2014

Eur J Org Chem

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An oxidative coupling of amines to give imines in ionic liquids (ILs) under metal‐free aerobic conditions has been developed. The high efficiency achievable in ILs is mechanistically explained in terms of activation of the starting materials (benzylamine and molecular oxygen) by an initial electron transfer, promoted by the ionic nature of the solvent. Reactivity data of variously p‐substituted benzylamines show a general deactivating effect, which would imply a change in the rate‐determining step in the reaction mechanism.

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Section: Introductionmentioning

confidence: 99%

Ionic‐Liquid‐Assisted Metal‐Free Oxidative Coupling of Amines To Give Imines

Monopoli¹,

Cotugno²,

Iannone³

et al. 2014

Eur J Org Chem

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“…In particular, MALDI MS has become a technique of considerable impact on many fi elds, from proteomics [ 11 , 12 ] to lipidomics [ 13 , 14 ] and, more recently, even metabolomics due to the introduction of new matrices such as ionic liquids [ 15 , 16 ], proton sponges [ 17 ] or aromatic amines [ 18 ], and metal nanoparticles [ 19 , 20 ].…”

Section: Food Analysis By Mass Spectrometrymentioning

confidence: 99%

Proteomic Analysis of Complex Protein Samples by MALDI–TOF Mass Spectrometry

Calvano

Ceglie

Zambonin

2014

Methods in Molecular Biology

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MALDI MS has become a technique of considerable impact on many fields, from proteomics to lipidomics, including polymer analysis and, more recently, even low molecular weight analytes due to the introduction of matrix-less ionization techniques (e.g., DIOS) or new matrices such as ionic liquids, proton sponges, and metal nanoparticles. However, protein identification by peptide mass fingerprint (PMF) still remains the main routine application. In the last few years, MALDI MS has played an emerging role in food chemistry especially in detection of food adulterations, characterization of food allergens, and investigation of protein structural modifications, induced by various industrial processes that could be detrimental for food quality and safety. Sample handling and pretreatment can be very different depending on the physical state, liquid or solid, of the analyzed matrices. Here, we describe simple protocols for protein extraction and MALDI MS analysis of liquid (milk) and solid (hazelnuts) samples taken as model. A classic approach based on a preliminary SDS gel electrophoresis separation followed by in-gel digestion and a faster approach based on in-solution digestion of whole samples are described and compared.

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“…[4,5] In the past decades, many methods have been developed for the synthesis of N-alkylated amines, including the employments of alcohols, alkylbromide, [31,32] nitriles, [33,34] aldehydes, [1] alkyl halides, [35][36][37][38][39] allyl and benzyl halides, [36,39] R-NH 2 ·HBr and alkyl bromides, [40] carboxylic acids [41] and dialkylboron triflates. [42] In recent years, organic azides have been considered to be valuable intermediates in the synthesis of N-alkylated anilines in spite of their explosive features.…”

Section: Introductionmentioning

confidence: 99%