An Introverted Bis‐Au Cavitand and Its Catalytic Dimerization of Terminal Alkynes

Endo, Naoki; Kanaura, Mao; Schramm, Michael; Iwasawa, Tetsuo

doi:10.1002/ejoc.201600362

Cited by 32 publications

(23 citation statements)

References 43 publications

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“…The authors also showed that the presence of two introverted Au atoms is quintessential for catalysis . Similar results were obtained with analogues of 11 having NMe 2 instead of OMe substituents on phosphorus …”

Section: Catalytic Chemistry With Cavitands Substituted With P Donorssupporting

confidence: 62%

The Use of Resorcinarene Cavitands in Metal‐Based Catalysis

et al. 2017

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Catalytic chemistry involving coordination complexes based on resorcinarene cavitands has been little explored in comparison to the many studies concerning the use of such ligands in classical coordination chemistry or host–guest chemistry. The potential utility of resorcinarene cavitands in catalysis arises essentially from two features: (1) their ability to function as ligands suitable for metal confinement and thus to make reactions either shape selective or to enhance their rates through supramolecular assistance by the receptor subunit; (2) their ability to enforce steric interactions with a coordinated metal center and thereby favor carbon–carbon bond forming reactions. To date, limited use has been made of cavitands as platforms for the attachment of different ligating sites, in particular for the generation of multifunctional ligands giving rise to anchimeric assistance in catalytic reactions. This review is intended to show the promise that exists in this area. As generic cavitands can be easily expanded to result in large bowl‐shaped structures as well as capsular containers, it may be anticipated that future work in this field will focus on the synthesis of sophisticated, metallated microreactors (possibly made water‐soluble) for highly selective transformations, including polymerizations.

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Section: Catalytic Chemistry With Cavitands Substituted With P Donorssupporting

confidence: 62%

The Use of Resorcinarene Cavitands in Metal‐Based Catalysis

et al. 2017

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“…Given the efficiency of the two quinoxaline walls in 2 , we then investigated the homodimerization reactions of 1‐octyne and 4‐phenyl‐1‐butyne in the presence of 2 , 3 , and 4 (Scheme ). Under the conditions outlined in Scheme , catalyst 1 mainly yielded an exo ‐methylene compound (i.e., 17 or 19 ): depending on the starting alkyne, the product included the corresponding isomer with an internal olefin (i.e., iso ‐ 17 or iso ‐ 19 ) . The results obtained with the use of 2 – 4 as catalysts are summarized in Table .…”

Section: Resultsmentioning

confidence: 99%

“…To compare more accurately the catalytic activities of 2 – 4 , we recorded the chemical yields and molar ratios of 19 / iso ‐ 19 by varying the temperature in the homodimerization of 4‐phenyl‐1‐butyne (Table ) . The reaction temperature was increased from room temperature to 110 °C.…”

Section: Resultsmentioning

confidence: 99%

Evaluation of the Reactivity of Metallocatalytic Cavities in the Dimerization of Terminal Alkynes

et al. 2016

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The effect of a metallocatalytic cavity flanked by aromatic rings on the catalytic dimerization of terminal alkynes was explored through a comparison with model catalysts that weakened the cavity. The diquinoxaline‐spanned resorcin[4]arene provided a definite compartment, in which the two Au centers enticed two alkynes to undergo the coupling reaction. We synthesized two kinds of model compounds in which one lacked two quinoxaline walls and the other had two pyrazine walls and found that these catalysts exhibited much lower reactivity. The two quinoxaline moieties proved to be quintessential for the catalytic event.

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“…A dinuclear version of the cavitand with two gold atoms opposite to each other was published shortly after (Figure ) ,. This dinuclear gold catalyst enabled dimerization of terminal alkynes to form conjugated enynes, whereas the mononuclear gold‐cavitand was unreactive in this reaction.…”

Section: Covalently Functionalized Catalystsmentioning

confidence: 99%

Gold Catalysis in (Supra)Molecular Cages to Control Reactivity and Selectivity

2018

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Gold catalysis has experienced a tremendous development over the past decades, and is nowadays widely used in organic synthesis to perform chemical transformations of π‐bond‐containing molecules. Catalyst development has been based mostly on ligand development and counter‐ion strategies. More recently, the encapsulation of gold catalysts in (supra)molecular cages was explored as a new way to control selectivity and reactivity of gold catalysts. In this review, we describe the cages that have been employed as hosts for gold complexes, along with their impact on the catalytic performance. Covalent and supramolecular approaches to encapsulate single metal complexes will be described and the impact on the catalytic performance will be discussed. Also, recent strategies to pre‐organize multiple metal centers will be discussed.

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An Introverted Bis‐Au Cavitand and Its Catalytic Dimerization of Terminal Alkynes

Cited by 32 publications

References 43 publications

The Use of Resorcinarene Cavitands in Metal‐Based Catalysis

The Use of Resorcinarene Cavitands in Metal‐Based Catalysis

Evaluation of the Reactivity of Metallocatalytic Cavities in the Dimerization of Terminal Alkynes

Gold Catalysis in (Supra)Molecular Cages to Control Reactivity and Selectivity

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