Halogen, Chalcogen, Pnictogen, and Tetrel Bonding in Non‐Covalent Organocatalysis: An Update

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(31)

Опубликована: Май 11, 2024

The use of noncovalent interactions based on electrophilic halogen, chalcogen, pnictogen, or tetrel centers in organocatalysis has gained noticeable attention. Herein, we provide an overview the most important developments last years with a clear focus experimental studies and catalysts which act via such non-transient interactions.

Язык: Английский

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Harnessing Multistep Chalcogen Bonding Activation in the α-Stereoselective Synthesis of Iminoglycosides

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(15), С. 10608 - 10620

Опубликована: Апрель 2, 2024

The use of noncovalent interactions (NCIs) has received significant attention as a pivotal synthetic handle. Recently, the exploitation unconventional NCIs gained considerable traction in challenging reaction manifolds such glycosylation due to their capacity facilitate entry into difficult-to-access sugars and glycomimetics. While investigations involving oxacyclic pyrano- or furanoside scaffolds are relatively common, methods that allow selective synthesis biologically important iminosugars comparatively rare. Here, we report phosphonochalcogenide (PCH) catalyze stereoselective α-iminoglycosylation iminoglycals with wide array glycosyl acceptors remarkable protecting group tolerance. Mechanistic studies have illuminated counterintuitive role catalyst serially activating both donor acceptor up/downstream stages through chalcogen bonding (ChB). dynamic interaction chalcogens substrates opens up new mechanistic opportunities based on iterative ChB engagement disengagement multiple elementary steps.

Язык: Английский

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Bidentate selenium-based chalcogen bond catalyzed cationic polymerization of p-methoxystyrene

Chemical Communications, Год журнала: 2024, Номер 60(10), С. 1321 - 1324

Опубликована: Янв. 1, 2024

Controllable cationic polymerization of p -methoxystyrene catalyzed by a chalcogen bond catalyst bis-selenonium salt.

Язык: Английский

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Telluronium‐Catalyzed Halogenation Reactions: Chalcogen‐Bond Activation of N‐Halosuccinimides and Catalysis

Chemistry - A European Journal, Год журнала: 2024, Номер 30(43)

Опубликована: Май 24, 2024

The ability of triaryltelluronium salts to interact with N-halosuccinimides (NXS) through chalcogen bonding (ChB) in the solid state and solution is demonstrated herein. Cocrystals bearing two CF

Язык: Английский

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Cationic Hypervalent Chalcogen Bond Catalysis on the Povarov Reaction: Reactivity and Stereoselectivity

Chemistry - A European Journal, Год журнала: 2024, Номер 30(24)

Опубликована: Фев. 19, 2024

Abstract Chalcogen bond catalysis, particularly cationic hypervalent chalcogen is considered to be an effective strategy for organocatalysis. In this work, the catalysis Povarov reaction between N‐benzylideneaniline and ethyl vinyl ether was investigated by density functional theory (DFT). The catalytic involves cycloaddition process proton transfer process, rate‐determining step process. Cationic tellurium derivatives bearing CF 3 F groups exhibit superior activity. For step, Gibbs free energy barrier decreases as positive electrostatic potential of catalysts increases. More importantly, has a strong linear correlation with in catalyst‐substrate complex. Furthermore, reactions include endo pathway exo pathway. C−H⋅⋅⋅π interaction substituent aryl ring contributes endo‐selectivity reaction. This research deeper understanding providing insights designing high performance.

Язык: Английский

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Nichtkovalente Organokatalyse mit Halogen‐, Chalkogen‐, Pniktogen‐ und Tetrelbrücken: neuere Entwicklungen

Angewandte Chemie, Год журнала: 2024, Номер 136(31)

Опубликована: Май 10, 2024

Abstract Die Anwendung nichtkovalenter Wechselwirkungen, welche auf elektrophilen Halogen‐, Chalkogen‐, Pniktogen‐ oder Tetrelzentren beruhen, hat in der Organokatalyse deutlich an Aufmerksamkeit gewonnen. Wir geben hier einen Überblick über die wichtigsten Entwicklungen letzten Jahre, mit einem Fokus experimentellen Studien und Katalysatoren, nicht‐transiente derartige Welchselwirkungen agieren.

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