Carbonyl Activation by Selenium‐ and Tellurium‐Based Chalcogen Bonding in a Michael Addition Reaction
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چکیده
منابع مشابه
Carbon–Halogen Bond Activation by Selenium‐Based Chalcogen Bonding
Chalcogen bonding is a little explored noncovalent interaction similar to halogen bonding. This manuscript describes the first application of selenium-based chalcogen bond donors as Lewis acids in organic synthesis. To this end, the solvolysis of benzhydryl bromide served as a halide abstraction benchmark reaction. Chalcogen bond donors based on a bis(benzimidazolium) core provided rate acceler...
متن کاملA halogen-bonding-catalyzed Michael addition reaction† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7cc07175b
Only a few studies on the use of halogen bonding in catalysis have been published so far. Herein, (benz)imidazolium-based halogen bond donors are used as catalysts in a Michael addition reaction. The most potent catalyst, a rigid atropisomer featuring two iodobenzimidazolium moieties, provided a rate acceleration versus a reference compound of ca. 50.
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The N···S chalcogen bond between SF4 and a series of alkyl and arylamines is examined via ab initio calculations. This bond is a strong one, with a binding energy that varies from a minimum of 7 kcal/mol for NH3 to 14 kcal/mol for trimethylamine. Its strength derives in large measure from charge transfer from the N lone pair into the σ*(SF) antibonding orbitals involving the two equatorial F at...
متن کاملCatalytic Carbon–Chlorine Bond Activation by Selenium‐Based Chalcogen Bond Donors
Chalcogen bonding is a noncovalent interaction based on electrophilic chalcogen substituents, which shares many similarities with the more well-known hydrogen and halogen bonding. Herein, the first application of selenium-based chalcogen bond donors in organocatalysis is described. Cationic bifunctionalized organoselenium compounds activate the carbon-chlorine bond of 1-chloroisochroman in a be...
متن کاملSupramolecular macrocycles reversibly assembled by Te…O chalcogen bonding
Organic molecules with heavy main-group elements frequently form supramolecular links to electron-rich centres. One particular case of such interactions is halogen bonding. Most studies of this phenomenon have been concerned with either dimers or infinitely extended structures (polymers and lattices) but well-defined cyclic structures remain elusive. Here we present oligomeric aggregates of het...
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ژورنال
عنوان ژورنال: Chemistry – A European Journal
سال: 2020
ISSN: 0947-6539,1521-3765
DOI: 10.1002/chem.201905057