Evaluation of tuned phosphorus cavitands on catalytic cross-dimerization of terminal alkynes

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

doi:10.1016/j.tetlet.2016.09.039

Cited by 16 publications

(11 citation statements)

References 18 publications

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“…The confinement created by 11 further limits the number of transition‐state geometries, this possibly being at the origin of the slightly higher selectivity found with 11 vs. 12 . 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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“…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%

“…[9] Sollogoub and co-workers developed a series of cyclodextrins with an N-heterocylic carbene (NHC) gold complex attached to the small rim pointing inside the cavity ( Figure 5). [29,30] Consequently, coordination of metals to the NHC leads to systems in which the metal atom is deeply buried inside the cavity, as proven by extensive NMR studies.…”

Section: Cyclodextrinsmentioning

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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“…The role of the cavitand itself remains open for exploration. 2‐wall bis‐gold cavitands and 2‐wall mono‐gold mono‐phosphorus oxide cavitands, followed quickly and these species point to a role of intermediate stabilization as well as the importance of correct spatial‐positioning. They have been added to a very recent review that encompasses earlier mentioned topics as well as the most recent approaches (e.g.…”

Section: Introductionmentioning

confidence: 99%

Au‐Cavitand Catalyzed Alkyne‐Acid Cyclizations

Schramm

2019

Eur J Org Chem

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Supramolecular cavitands that contain inwardly directed functional groups have yielded specialized transformations and trapping of reactive intermediates. A recently reported 3‐wall Au cavitand provides exciting opportunities for supramolecular catalysis. In this study, a variety of substituted γ‐alkynoic acids were reacted to give lactones. The interaction of peripheral “R” groups revealed differential catalyst behavior. Extremely large and small groups reacted with appreciable rate. Intermediate sized groups however, slowed significantly: giving support that size‐specific binding is at play when using cavitands as a scaffold for gold catalysis. These results serve as some of the first evidence of the interplay between substrate and cavitand interior in the catalytic sphere.

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Evaluation of tuned phosphorus cavitands on catalytic cross-dimerization of terminal alkynes

Cited by 16 publications

References 18 publications

The Use of Resorcinarene Cavitands in Metal‐Based Catalysis

The Use of Resorcinarene Cavitands in Metal‐Based Catalysis

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

Au‐Cavitand Catalyzed Alkyne‐Acid Cyclizations

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