Imidazole-Catalyzed Henry Reactions in Aqueous Medium

Phukan, Mridula; Borah, Kunal; Borah, Ruli

doi:10.1080/00397910802045592

Cited by 18 publications

(8 citation statements)

References 15 publications

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“…With 0.25 mmol of imidazole, it yielded only 60% of 2-nitroalkanol within 5 minutes (entry 1) as monitored by TLC. Interestingly, 0.25 mmol of imidazole is however found to be sufficient to complete most of the reaction of the aromatic aldehyde within a short period of time in the aqueous phase as we have reported recently (30). Most probably, in solid state this amount of catalyst is not sufficient to catalyze the Henry reaction.…”

Section: Resultsmentioning

confidence: 85%

“…In continuation of our research interest in the development of environmentally benign syntheses, recently, we have reported imidazole, a suitable base for catalyzing the Henry reaction in aqueous medium (30) and organic solvent which prevents side reactions. The catalyst in aqueous medium was recyclable several times without lost of catalytic activity.…”

Section: Introductionmentioning

confidence: 99%

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Henry reaction in environmentally benign methods using imidazole as catalyst

Phukan

Borah

2009

Green Chemistry Letters and Reviews

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Imidazole has been found to be an efficient Lewis base catalyst for the synthesis of 2-nitroalkanols from nitroaldol reaction in aqueous medium as well as using solvent-free grinding methods. In both cases, the products have been found in good to moderate yields without formation of any side product. Recycling of the catalyst is also possible with imidazole containing aqueous phase reaction medium (after extraction of product).

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Section: Resultsmentioning

confidence: 85%

Section: Introductionmentioning

confidence: 99%

Henry reaction in environmentally benign methods using imidazole as catalyst

Phukan

Borah

2009

Green Chemistry Letters and Reviews

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“…o ‐Hydroxyaromatic‐ α , β ‐unsaturated ketones 1 and α ‐nitroketone 2 were prepared as per previously reported methods.…”

Section: Methodsmentioning

confidence: 99%

Organocatalytic Asymmetric Michael–Acyl Transfer Reaction of α‐Nitroketones with 2‐Hydroxybenzylidene Ketones

Maity

Pan

2019

Eur J Org Chem

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“…As a fundamental CC bond forming process, the Henry reaction is an interesting system to study . Observed benefits for performing this reaction in water include short reaction times, facile purification, and reduced side‐product formation . Because the reaction is initiated by base‐catalyzed proton abstraction from the nitroalkane, most theoretical investigations have studied the reaction between the resultant nitroalkane anion and an aldehyde .…”

Section: The Henry Reactionmentioning

confidence: 99%

Application of a BOSS—Gaussian interface for QM/MM simulations of Henry and methyl transfer reactions

et al. 2015

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Hybrid quantum mechanics and molecular mechanics (QM/MM) computer simulations have become an indispensable tool for studying chemical and biological phenomena for systems too large to treat with quantum mechanics alone. For several decades, semi-empirical QM methods have been used in QM/MM simulations. However, with increased computational resources, the introduction of ab initio and density function methods into on-the-fly QM/MM simulations is being increasingly preferred. This adaptation can be accomplished with a program interface that tethers independent QM and MM software packages. This report introduces such an interface for the BOSS and Gaussian programs, featuring modification of BOSS to request QM energies and partial atomic charges from Gaussian. A customizable C-shell linker script facilitates the inter-program communication. The BOSS–Gaussian interface also provides convenient access to Charge Model 5 (CM5) partial atomic charges for multiple purposes including QM/MM studies of reactions. In this report, the BOSS–Gaussian interface is applied to a nitroaldol (Henry) reaction and two methyl transfer reactions in aqueous solution. Improved agreement with experiment is found by determining free-energy surfaces with MP2/CM5 QM/MM simulations than previously reported investigations employing semiempirical methods.

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Imidazole-Catalyzed Henry Reactions in Aqueous Medium

Cited by 18 publications

References 15 publications

Henry reaction in environmentally benign methods using imidazole as catalyst

Henry reaction in environmentally benign methods using imidazole as catalyst

Organocatalytic Asymmetric Michael–Acyl Transfer Reaction of α‐Nitroketones with 2‐Hydroxybenzylidene Ketones

Application of a BOSS—Gaussian interface for QM/MM simulations of Henry and methyl transfer reactions

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