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

Jovanovic, Dragana; Poliyodath Mohanan, Meghana; Huber, Stefan M.

doi:10.1002/anie.202404823

Angew Chem Int Ed

2024

DOI: 10.1002/anie.202404823

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

Dragana Jovanovic,

Meghana Poliyodath Mohanan,

Stefan M. Huber

Abstract: 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 on the most important developments in the last years with a clear focus on experimental studies and on catalysts which act via such non‐transient interactions.

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Cited by 2 publications

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Recent Developments in Selenylation of Alkynes

Xu,

Huang,

et al. 2024

Adv Synth Catal

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Alkynes are simple yet important organic feedstocks. The selenylation of alkynes is able to produce complex selenium‐containing compounds in a facile way. Although there are some reviews about the selenylation of alkynes, most of them focus on one specific reaction or what types of products that can be obtained. There is a lack of attention given to the various uses of different selenium reagents and their mechanisms. This review mainly focuses on recent advances (2013‐2023) based on diverse selenium reagents. Mechanisms and how the added reagents work will be discussed. Different reaction types, including difunctionalization, Se‐annulation, spiro‐cyclization, C‐Se coupling, click reaction will be recorded in this review. The regioselectivity can be achieved through various mechanisms, including radicals, seleniraniums or electrophilic cyclization. We hope it will do help for future research in this area.

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Recent Developments in Selenylation of Alkynes

Xu,

Huang,

et al. 2024

Adv Synth Catal

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

Groslambert,

Pale,

Mamane

2024

Chemistry A European J

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The ability of triaryltelluronium salts to interact with N‐halosuccinimides (NXS) through chalcogen bonding (ChB) in the solid state and in solution is demonstrated herein. Cocrystals of the triaryltelluronium bearing two CF3 electron‐withdrawing groups per aryl ring with N‐chloro‐, N‐bromo‐ and N‐iodosuccinimide (respectively NCS, NBS and NIS) were analyzed by X‐ray diffraction, evidencing a ChB between tellurium and the carbonyl group of NXS. This ChB was confirmed in solution by NMR spectroscopy, especially by 125Te NMR titration experiment, which allowed the determination of the association constant (Ka) between the telluronium and NBS. The so‐obtained Ka value of 17.3 ± 0.6 M‐1 indicated a moderate interaction in solution because of the competitive role of the solvent. The strength of the Te‐‐‐O ChB was however sufficient enough to promote the catalytic halofunctionalization of aromatics and of alkenes such as the intra‐ and intermolecular haloalkoxylation and haloesterification of alkenes.

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

Cited by 2 publications

References 188 publications

Recent Developments in Selenylation of Alkynes

Recent Developments in Selenylation of Alkynes

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

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