Chiral derivatives of 1,2-benzenedisulfonimide as efficient Brønsted acid catalysts in the Strecker reaction

Barbero, Margherita; Cadamuro, Silvano; Dughera, Stefano; Torregrossa, Roberta

doi:10.1039/c4ob00552j

Cited by 23 publications

(6 citation statements)

References 52 publications

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“…The poor reactivity observed under photochemical conditions confirmed that the reaction occurs preferentially under thermal/chemical activation. In another recent article, Barbero and Dughera have utilized arenediazonium o‐ benzenedisulfonimides as the coupling partners for gold‐catalyzed Heck coupling reactions (Scheme ) …”

Section: Oxidant‐free Approaches For Homogeneous Au‐catalyzed Cross‐c...mentioning

confidence: 99%

Gold‐Catalyzed Cross‐Coupling Reactions: An Overview of Design Strategies, Mechanistic Studies, and Applications

Nijamudheen

Datta

2019

Chemistry A European J

153

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Transition-metal-catalyzed cross-couplingr eactions are central to many organic synthesis methodologies. Traditionally,P d, Ni, Cu, and Fe catalysts are used to promote these reactions. Recently,m any studies have showedt hat both homogeneous and heterogeneous Au catalysts can be used for activating selective cross-coupling reactions.H ere, an overview of the past studies, current trends, andf uture directions in the field of gold-catalyzed coupling reactions is presented.D esign strategiest oa ccomplish selective homocoupling and cross-coupling reactions under both homogeneous and heterogeneous conditions, computational and ex-perimental mechanistic studies, and their applicationsi nd iverse fields are critically reviewed. Specific topics covered are:o xidant-assisted and oxidant-free reactions;s train-assisted reactions;d ual Au and photoredoxc atalysis;b imetallic synergistic reactions;m echanismso fr eductivee limination processes;e nzyme-mimicking Au chemistry;c lustera nd surface reactions;a nd plasmonic catalysis. In the relevant sections, theoretical and computational studies of Au I /Au III chemistry are discussed and the predictionsf rom the calculationsa re compared with the experimental observations to derive useful design strategies.A. Nijamudheen earnedh is PhD from IACS, Kolkata,i n2 015. Currently,h ei sapostdoctoral researcher atF loridaS tate University.H is researchi nterests are in computational catalysis, solar energym aterials, and beyond Li-ion battery technologies.Ayan Dattai sc urrently aP rofessor at IACS, Kolkata.H is research interests include theoretical and computational studieso ft ransitionmetal-catalyzed reactions,o pto-electronic properties of organic and solid-statem aterials, and the design of renewableenergymaterials. He has won several awards including the DST-SERB Distinguished Investigator Award (DIA) in 2019.

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Section: Oxidant‐free Approaches For Homogeneous Au‐catalyzed Cross‐c...mentioning

confidence: 99%

Gold‐Catalyzed Cross‐Coupling Reactions: An Overview of Design Strategies, Mechanistic Studies, and Applications

Nijamudheen

Datta

2019

Chemistry A European J

153

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“…Dughera and co-workers synthesized a sulfonimide derivative with an atropisomeric p-terphenyl structure (Scheme 80). 87 The C 2 chiral compound catalyzed the three-component Strecker reaction of aromatic aldehydes or methylketones, aniline derivatives, and (CH 3 ) 3 SiCN to give the aminonitrile products in moderate yield and in up to 97% ee.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Asymmetric Cyanation Reactions

2016

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Catalytic asymmetric cyanations of prochiral unsaturated compounds affording the corresponding nitrile products in high enantiomeric excess (≥90% in general) are summarized in this review. The nucleophilic cyanide addition onto aldehydes, ketones, and imines is promoted by chiral metal complexes and organocatalysts. Recent progress in asymmetric conjugate cyanation of α,β-unsaturated carbonyl compounds is also discussed. The asymmetric cyanation of unactivated alkenes is catalyzed by chiral transition-metal complexes. Current topics of intramolecular carbocyanation and aminocyanation in addition to the traditional hydrocyanation are reviewed.

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“…In other cases, the use of solvents as dichloromethane, toluene or chloroform, and temperatures higher than rt was required. Similarly, soluble catalysts, such as o- benzenedisulfonimide, and sulfonic acid based nanoreactors have also been employed in larger catalyst loadings. InPF-110, even without any solvent, also outperforms previously reported MOFs tested in the same reaction, as shown in SI Table 5.2.…”

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confidence: 99%

A Mesoporous Indium Metal–Organic Framework: Remarkable Advances in Catalytic Activity for Strecker Reaction of Ketones

et al. 2016

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With the aim of developing new highly porous, heterogeneous Lewis acid catalysts for multicomponent reactions, a new mesoporous metal-organic framework, InPF-110 ([In3O(btb)2(HCOO)(L)], (H3btb = 1,3,5-tris(4-carboxyphenyl)benzene acid, L = methanol, water, or ethanol), has been prepared with indium as the metal center. It exhibits a Langmuir surface area of 1470 m(2) g(-1), and its structure consists of hexagonal pores with a 2.8 nm aperture, which allows the diffusion of multiple substrates. This material presents a large density of active metal sites resulting in outstanding catalytic activity in the formation of substituted α-aminonitriles through the one-pot Strecker reaction of ketones. In this respect, InPF-110 stands out compared to other catalysts for this reaction due to the small catalyst loadings required, and without the need for heat or solvents. Furthermore, X-ray single crystal diffraction studies clearly show the framework-substrate interaction through coordination to the accessible indium sites.

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Chiral derivatives of 1,2-benzenedisulfonimide as efficient Brønsted acid catalysts in the Strecker reaction

Cited by 23 publications

References 52 publications

Gold‐Catalyzed Cross‐Coupling Reactions: An Overview of Design Strategies, Mechanistic Studies, and Applications

Gold‐Catalyzed Cross‐Coupling Reactions: An Overview of Design Strategies, Mechanistic Studies, and Applications

Catalytic Asymmetric Cyanation Reactions

A Mesoporous Indium Metal–Organic Framework: Remarkable Advances in Catalytic Activity for Strecker Reaction of Ketones

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