Rate Enhancement of the Morita—Baylis—Hillman Reaction Through Mechanochemistry.

Mack, James; Shumba, Maxwell

doi:10.1002/chin.200733075

Cited by 7 publications

(7 citation statements)

References 1 publication

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“…The technique applied to MBH reactions represented one of the fastest options producing yields ranging from 28 to 98% under neat conditions. Furthermore, the technique is an example of green chemistry due to no solvents are required [ 41 ].…”

Section: Reaction Times Yield and Stereochemistry Of Mbh Reactionmentioning

confidence: 99%

The Morita-Baylis-Hillman Reaction: Insights into Asymmetry and Reaction Mechanisms by Electrospray Ionization Mass Spectrometry

2009

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This short review presents new insights on the mechanism and online monitoring using electrospray ionization tandem mass spectrometry (ESI-MS/MS) of Morita-Baylis-Hillman (MBH) reactions. MBH reactions are versatile carbon-carbon organocatalyzed bond forming reactions, making them environmentally friendly due to general organocatalysts employed. The organocatalyst behavior, which controls the transition state and thus the enantioselectivities in the obtained products, is very important in the performance of asymmetric MBH transformations. Some recent techniques and advances in asymmetric transformations are reviwed, as well as online reaction monitoring and analysis of the reaction intermediates. The mechanism accepted nowadays is also review through the insights gained from the use of ESI-MS/MS techniques.

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Section: Reaction Times Yield and Stereochemistry Of Mbh Reactionmentioning

confidence: 99%

The Morita-Baylis-Hillman Reaction: Insights into Asymmetry and Reaction Mechanisms by Electrospray Ionization Mass Spectrometry

2009

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“…14 Beyond porous materials synthesis, ball milling has been used to promote catalysis of C−H bond functionalization/amination 15,16 and in the generation of Baylis−Hillman products. 17 More relevant to our work, MS has been used in the synthesis of perovskite materials (ABO 3 ), which would normally require 800−1200 °C. 6,18,19 The local heating produced by mechanochemistry (accelerating diffusion by mechanical energy and frictional heating) leads to a near instantaneous quenching of induced atomic diffusion that enables the preparation of metastable phases, which has inspired us to study the solid-state synthesis of entropystabilized mixed metal oxides.…”

mentioning

confidence: 99%

Mechanochemical Synthesis of High Entropy Oxide Materials under Ambient Conditions: Dispersion of Catalysts via Entropy Maximization

Chen

Lin

Zhang

et al. 2019

ACS Materials Lett.

187

103

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The solid-solution metal oxide (NiMgCuZnCo)O is the first known high-entropy (HE) metal oxide synthesized, forming a poster child of the emerging high-entropy oxide materials, which is derived from high-temperature synthesis methodologies (>900 °C). In this work, we report the mechanochemical synthesis of this known HE metal oxide (NiMgCuZnCo)O under ambient conditions. The advantage of this approach was further demonstrated by the introduction of up to 5 wt % noble metal into (NiMgCuZnCo)O, as single atoms or nanoclusters, which showed good stability at high temperature and produced a high catalytic activity in the hydrogenation of atmospheric CO 2 to CO. The latter work demonstrated the unique advantage of using HE materials to disperse catalysis centers.

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“…The Morita-Baylis-Hillman (MBH) reaction possesses the two most important requirements: atom economy and generation of multi-functional groups, and, therefore, it has attracted many synthetic chemists to explore different aspects of the MBH reaction [ 46 , 47 , 48 , 49 , 50 ]. As for the development of new reaction media [ 51 , 52 , 53 , 54 ], Basavaiah and Reddy have already demonstrated the usefulness of silica gel as a reaction medium for this reaction [ 51 ]. Therefore, we simply describe here a few additional results previously obtained by us [ 55 ].…”

Section: Resultsmentioning

confidence: 99%

Silica Gel-Mediated Organic Reactions under Organic Solvent-Free Conditions

et al. 2012

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Silica gel was found to be an excellent medium for some useful organic transformations under organic solvent-free conditions, such as (1) the Friedel-Crafts-type nitration of arenes using commercial aqueous 69% nitric acid alone at room temperature, (2) one-pot Wittig-type olefination of aldehydes with activated organic halides in the presence of tributyl- or triphenylphosphine and Hunig’s base, and (3) the Morita-Baylis-Hillman reaction of aldehydes with methyl acrylate. After the reactions, the desired products were easily obtained in good to excellent yields through simple manipulation.

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Rate Enhancement of the Morita—Baylis—Hillman Reaction Through Mechanochemistry.

Cited by 7 publications

References 1 publication

The Morita-Baylis-Hillman Reaction: Insights into Asymmetry and Reaction Mechanisms by Electrospray Ionization Mass Spectrometry

The Morita-Baylis-Hillman Reaction: Insights into Asymmetry and Reaction Mechanisms by Electrospray Ionization Mass Spectrometry

Mechanochemical Synthesis of High Entropy Oxide Materials under Ambient Conditions: Dispersion of Catalysts via Entropy Maximization

Silica Gel-Mediated Organic Reactions under Organic Solvent-Free Conditions

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