Convergent Ditopic Receptors Enhance Anion Binding upon Alkali Metal Complexation for Catalyzing the Ritter Reaction

Kang, Kang; Lohrman, Jessica; Nagarajan, Sangaraiah; Chen, Lixi; Deng, Pengchi; Shen, Xiaotao; Fu, Kuirong; Feng, Wen; Johnson, Darren W.; Yuan, Lihua

doi:10.1021/acs.orglett.8b03778

Cited by 26 publications

(13 citation statements)

References 65 publications

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“…These issuesh ave inspiredv ery recent efforts toward the designo fm ore efficient and selectivea nion-binding catalysts basedo nm ultidentate hydrogen-bonding supramolecular structures. [2][3][4] Among them, macrocyclic bisthiourea or polyamide structures, [4] as well as triazole-based supramolecular catalysts can be highlighted ( Figure 1). [5][6][7] In particular,t riazole HB-donor derivativesh ave recently attracted great attention due to the severalp olarized sites pres- Figure 1.…”

Section: Introductionmentioning

confidence: 99%

Insight into the Folding and Cooperative Multi‐Recognition Mechanism in Supramolecular Anion‐Binding Catalysis

Piekarski

Steinforth

Gómez‐Martínez

et al. 2020

Chemistry A European J

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H-bond donor catalysts able to modulate the reactivity of ionic substrates for asymmetric reactions have gained great attention in the past years, leadingt ot he development of cooperative multidentate H-bonding supramolecular structures. However,t here is still al ack of understanding of the forces driving the ion recognition and catalytic performance of these systems. Herein, insight into the cooperativity nature, anion binding strength, and folding mechanism of am odel chiral triazole catalysti sp resented. Our combinede xperimentala nd computational study revealedthat multi-interaction catalysts exhibiting weak binding energies (% 3-4 kcal mol À1)c an effectively recognize ionic substrates and induce chirality,w hile strong dependencies on the temperature and solventw ere quantified. These results are key for the future design of catalystsw ith optimal anion bindings trength and catalytica ctivity in target reactions.

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Section: Introductionmentioning

confidence: 99%

Insight into the Folding and Cooperative Multi‐Recognition Mechanism in Supramolecular Anion‐Binding Catalysis

Piekarski

Steinforth

Gómez‐Martínez

et al. 2020

Chemistry A European J

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“…The combination of anion-binding catalysis and supramolecular chemistry is a fairly new arisen field, with a set number of notable examples [79][80][81][82][83]. Next to thioureas, investigations in this area of anion binding were also conducted for other catalytic systems.…”

Section: Non-thiourea-based Supramolecular Catalystsmentioning

confidence: 99%

Halides as versatile anions in asymmetric anion-binding organocatalysis

Schifferer¹,

Stinglhamer²,

Kaur³

et al. 2021

Beilstein J. Org. Chem.

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This review intends to provide an overview on the role of halide anions in the development of the research area of asymmetric anion-binding organocatalysis. Key early elucidation studies with chloride as counter-anion confirmed this type of alternative activation, which was then exploited in several processes and contributed to the advance and consolidation of anion-binding catalysis as a field. Thus, the use of the halide in the catalyst–anion complex as both a mere counter-anion spectator or an active nucleophile has been depicted, along with the new trends toward additional noncovalent contacts within the HB-donor catalyst and supramolecular interactions to both the anion and the cationic reactive species.

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“…[65] In 2019, Kang and co-workers designed catalyst for the Ritter reaction between acetonitrile 47 and (bromomethylene) dibenzene 147 in dichloromethane solvent at room temperature, which leads to the synthesis of N-banzhydrylacetamide 149 (Scheme 64). [66] The mechanism proceeds through the interaction of the catalyst system with (bromomethylene)dibenzene 147 to yield intermediate 150. ○C (Scheme 66).…”

Section: Using Alkyl or Aryl Halides As Starting Materialsmentioning

confidence: 99%

“…In 2019, Kang and co‐workers designed catalyst for the Ritter reaction between acetonitrile 47 and (bromomethylene)dibenzene 147 in dichloromethane solvent at room temperature, which leads to the synthesis of N ‐banzhydrylacetamide 149 (Scheme 64). [66] …”

Section: Application Of the Non‐classical Ritter Reaction In The Syntmentioning

confidence: 99%

Recent Applications of Ritter Reactions in Organic Syntheses

2020

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The Ritter reactions are an important Classes of organic reactions in the synthesis of heterocycles and linear amides. Ritter reaction products are pyridine, quinazolinone, and other heterocyclic structures, which have different biological activities such as antibacterial and antivirous application from 2017 to 2020. Furthermore, the Ritter reaction in the synthesis of linear amides is evaluated from 2015 to 2020 in this review. Linear amides are essential components in drug molecules which are difficult to synthesize by conventional methods but can be synthesized through the Ritter reaction.

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Convergent Ditopic Receptors Enhance Anion Binding upon Alkali Metal Complexation for Catalyzing the Ritter Reaction

Cited by 26 publications

References 65 publications

Insight into the Folding and Cooperative Multi‐Recognition Mechanism in Supramolecular Anion‐Binding Catalysis

Insight into the Folding and Cooperative Multi‐Recognition Mechanism in Supramolecular Anion‐Binding Catalysis

Halides as versatile anions in asymmetric anion-binding organocatalysis

Recent Applications of Ritter Reactions in Organic Syntheses

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