Nichtkovalente Organokatalyse mit Halogen‐, Chalkogen‐, Pniktogen‐ und Tetrelbrücken: neuere Entwicklungen DOI Creative Commons
Dragana Jovanovic,

Meghana Poliyodath Mohanan,

Stefan M. Huber

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(31)

Published: May 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.

Halogen, Chalcogen, Pnictogen, and Tetrel Bonding in Non‐Covalent Organocatalysis: An Update DOI Creative Commons
Dragana Jovanovic,

Meghana Poliyodath Mohanan,

Stefan M. Huber

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(31)

Published: May 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.

Language: Английский

Citations

27
Harnessing Multistep Chalcogen Bonding Activation in the α-Stereoselective Synthesis of Iminoglycosides DOI Creative Commons

Caiming Wang,

Anna Krupp, Carsten Strohmann

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(15), P. 10608 - 10620

Published: April 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.

Language: Английский

Citations

13
Bidentate selenium-based chalcogen bond catalyzed cationic polymerization of p-methoxystyrene DOI

Luya Cao,

Hao Chen, Hongjun Fu

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(10), P. 1321 - 1324

Published: Jan. 1, 2024

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

Language: Английский

Citations

5
Telluronium‐Catalyzed Halogenation Reactions: Chalcogen‐Bond Activation of N‐Halosuccinimides and Catalysis DOI Creative Commons

Loïc Groslambert,

Patrick Pale, Victor Mamane

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(43)

Published: May 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

Language: Английский

Citations

5
Cationic Hypervalent Chalcogen Bond Catalysis on the Povarov Reaction: Reactivity and Stereoselectivity DOI
Chang Zhao, Ying Li, Yanjiang Wang

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(24)

Published: Feb. 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.

Language: Английский

Citations

4
Nichtkovalente Organokatalyse mit Halogen‐, Chalkogen‐, Pniktogen‐ und Tetrelbrücken: neuere Entwicklungen DOI Creative Commons
Dragana Jovanovic,

Meghana Poliyodath Mohanan,

Stefan M. Huber

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(31)

Published: May 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.

Citations

2