Modular synthesis of cyclic β-difluoroamines

Fluorine-containing saturated nitrogen heterocycles are very attractive structures in medicinal and biological chemistry because fluorine can be used to tune conformation as well as key properties such as basicity and bioavailability. At present cyclic fluorinated amines are accessed using hazardous...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2024-07, Vol.6 (6), p.771-774
Hauptverfasser: Charlesworth, Natalie G, Arunprasath, Dhanarajan, Graham, Mark A, Argent, Stephen P, Datsenko, Oleksandr P, Mykhailiuk, Pavel K, Denton, Ross M
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Sprache:eng
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Zusammenfassung:Fluorine-containing saturated nitrogen heterocycles are very attractive structures in medicinal and biological chemistry because fluorine can be used to tune conformation as well as key properties such as basicity and bioavailability. At present cyclic fluorinated amines are accessed using hazardous reagents such as DAST or by lengthy synthesis routes. Here we report a modular two-step synthesis of cyclic β-fluoroalkyl amines using a photoredox-catalysed cyclisation/hydrogen atom transfer reaction of bromodifluoroethylamines. We report a new synthesis of cyclic β-fluoroalkyl amines using a photoredox-catalysed cyclisation which can be run in batch and flow-mode.
ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/d4cc00640b