On the mechanism of the aza-Morita–Baylis–Hillman reaction: ESI-MS interception of a unique new intermediate

Regiani, Thaís; Santos, Vanessa G.; Godoi, Marla Narciso; Vaz, Boniek G.; Eberlin, Marcos N.; Coelho, Fernando

doi:10.1039/c1cc10678c

Cited by 43 publications

(17 citation statements)

References 40 publications

(19 reference statements)

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“…The ability to identify transient intermediates is a significant advantage of MS, with ESI seeing particular use for this purpose . For example, ESI‐MS was used to intercept a short‐lived bis‐sulfonamide intermediate that aided in the interpretation of the reaction mechanism for the Morita‐Baylis‐Hillman reaction …”

Section: Methodsmentioning

confidence: 99%

Accelerated hydrazone formation in charged microdroplets

Bain

Pulliam

Ayrton

et al. 2016

Rapid Commun. Mass Spectrom.

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Reaction acceleration in droplets is attributed to solvent evaporation leading to increased surface to volume ratios. An acceleration factor of 10(4) , measured relative to the bulk reaction at short times, is readily achieved by simply increasing the droplet distance of flight showing that the same ionization source can be used to monitor reactions with or without acceleration. Copyright © 2016 John Wiley & Sons, Ltd.

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Section: Methodsmentioning

confidence: 99%

Accelerated hydrazone formation in charged microdroplets

Bain

Pulliam

Ayrton

et al. 2016

Rapid Commun. Mass Spectrom.

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“…[7] Examples of reactions catalysed by these metals include Friedel-Crafts acylations, [8] Michael additions, [9,10] aldol condensations [11] and cycloadditions. [18,19,28,29,[20][21][22][23][24][25][26][27] Electrospray ionization mass spectrometry (ESI-MS) is a highly sensitive technique for monitoring complex reaction mixtures. [17] The growing use and applications of lanthanides as catalysts calls for detailed understanding of their speciation in solution and their reactivity modes.…”

Section: Introductionmentioning

confidence: 99%

The Intermediates in Lewis Acid Catalysis with Lanthanide Triflates

Tripodi¹,

Correra

Angolini

et al. 2019

Eur J Org Chem

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Lanthanide triflates are effective Lewis acid catalysts in reactions involving carbonyl compounds due to their high oxophilicity and water stability. Despite the growing interest, the identity of the catalytic species formed in lanthanide catalysed reactions is still unknown. We have therefore used mass spectrometry and ion spectroscopy to intercept and characterize the intermediates in a reaction catalysed by ytterbium and dysprosium triflates. We were able to identify a number of lanthanide intermediates formed in a simple condensation reaction between a C‐acid and an aldehyde. Results show correlation between the reactivity of lanthanide complexes and their charge state and suggest that the triply charged complexes play a key role in lanthanide catalysed reactions. Spectroscopic data of the gaseous ions accompanied by theoretical calculations reveal that the difference between catalytic efficiencies of ytterbium and dysprosium ions can be explained by their different electrophilicity.

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“…In this sense, Santos et al 28 describe the inuence of using a derivative imidazolium IL as a solvent in MBH reaction rate between methyl acrylate and benzaldehyde. The reaction performed 14.1 times faster in ILs than in acetonitriles.…”

Section: -27mentioning

confidence: 99%

Amino acid ionic liquids as catalysts in a solvent-free Morita–Baylis–Hillman reaction

et al. 2018

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In the present work, we describe the preparation of ten amino acid ionic liquids (AAILs) formed from ammonium salts as cations, derivatives of glycerol, and natural amino acids as anions. All of them are viscous oils, colorless or pale yellow, and hygroscopic at room temperature. They have appreciable solubility in many protic and aprotic polar solvents. The AAILs were used as catalysts in a Morita-BaylisHillman (MBH) reaction. The ionic liquids derivative from L-proline and L-histidine demonstrated the ability to catalyze the reaction between methyl vinyl ketone and aromatic aldehydes differently substituted in the absence of an additional co-catalyst under organic solvent-free conditions. The AAIL derivatives from L-valine, L-leucine, and L-tyrosine catalyzed the MBH reaction only in the presence of imidazole. The MBH adducts were obtained in moderate to good yields. Although the catalytic site in the ILs was in its enantiomerically pure form, all the MBH adducts were obtained in their racemic form.

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On the mechanism of the aza-Morita–Baylis–Hillman reaction: ESI-MS interception of a unique new intermediate

Cited by 43 publications

References 40 publications

Accelerated hydrazone formation in charged microdroplets

Accelerated hydrazone formation in charged microdroplets

The Intermediates in Lewis Acid Catalysis with Lanthanide Triflates

Amino acid ionic liquids as catalysts in a solvent-free Morita–Baylis–Hillman reaction

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