Gas‐phase Diels–Alder cycloaddition reaction in the presence of methanol and water vapor

Gholami, Mohammad Reza; Talebi, B. A.

doi:10.1002/poc.577

Cited by 7 publications

(2 citation statements)

References 19 publications

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“…In the field of noncovalent organocatalysis, HB plays an important role, , and several examples of HB donor catalysts have been reported. ,− Taking into account the similarities between HB and XB, in particular for their effective use in anion recognition, ,,,, many researchers started to investigate the possible use of XB donor molecules as catalysts in organic synthesis. However, it appeared immediately clear that the potential of the XB in this field may arise mainly from the peculiarities of halogen-bonded systems compared to related systems based on HB .…”

Section: Functional Systemsmentioning

confidence: 99%

The Halogen Bond

et al. 2016

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The halogen bond occurs when there is evidence of a net attractive interaction between an electrophilic region associated with a halogen atom in a molecular entity and a nucleophilic region in another, or the same, molecular entity. In this fairly extensive review, after a brief history of the interaction, we will provide the reader with a snapshot of where the research on the halogen bond is now, and, perhaps, where it is going. The specific advantages brought up by a design based on the use of the halogen bond will be demonstrated in quite different fields spanning from material sciences to biomolecular recognition and drug design.

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Section: Functional Systemsmentioning

confidence: 99%

The Halogen Bond

et al. 2016

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“…There are several key experimental and computational findings that provide a rational basis for the design of a metal-free, hydrogen-bonding based catalytic system that is applicable to the Diels-Alder reaction of a diene with an electron deficient a,b-unsaturated carbonyl compound. First of all, water itself does have a significant effect on many reactions, in particular, the Diels-Alder reaction (Scheme 1); 16 there are several vividly debated reasons for this acceleration (solvent polarity, hydrophobicity, internal pressure (note that this effect is often misunderstood and apparently mixed up with cohesive energy density) etc. ), 17,18 but we will focus on the explicit interactions to derive a hydrogen-bonding catalyst motif.…”

Section: Catalysts and Reactionsmentioning

confidence: 99%

Metal-free organocatalysis through explicit hydrogen bonding interactions

2003

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The metal (ion)-free catalysis of organic reactions is a contemporary challenge that is just being taken up by chemists. Hence, this field is in its infancy and is briefly reviewed here, along with some rough guidelines and concepts for further catalyst development. Catalysis through explicit hydrogen bonding interactions offers attractive alternatives to metal (ion)-catalyzed reactions by combining supramolecular recognition with chemical transformations in an environmentally benign fashion. Although the catalytic rate accelerations relative to uncatalyzed reactions are often considerably less than for the metal (ion)-catalyzed variants, this need not be a disadvantage. Also, owing to weaker enthalpic binding interactions, product inhibition is rarely a problem and hydrogen bond additives are truly catalytic, even in water.

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Halogen Bonds in Organic Synthesis and Organocatalysis

Schindler

Huber

2014

Topics in Current Chemistry

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In contrast to hydrogen bonding, halogen bonding has so far found very little use in organic synthesis and organocatalysis. Although there are multiple reports on the use of elemental iodine in a wide range of organic reactions, the understanding of the actual mode of activation in these cases is very rudimentary. Recently, first proof-of-principle reactions have been established towards the use of carbon-based halogen-bond donors as activators or organocatalysts. These halogen-based Lewis acids offer more structural variety and potential than elemental iodine itself, and the mode of activation is better understood. Yet, the reported cases still only cover simple benchmark reactions, and there is a clear need for further and more complex applications.

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Gas‐phase Diels–Alder cycloaddition reaction in the presence of methanol and water vapor

Cited by 7 publications

References 19 publications

The Halogen Bond

The Halogen Bond

Metal-free organocatalysis through explicit hydrogen bonding interactions

Halogen Bonds in Organic Synthesis and Organocatalysis

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