Energy Transfer Catalysis Enabled 2,2,2‐Trifluoroethoxy‐Amination of Olefins DOI Creative Commons
Floriane Doche, Thibault Gallavardin, Thomas Poisson

и другие.

ChemistryEurope, Год журнала: 2025, Номер unknown

Опубликована: Май 6, 2025

A thioxanthone‐catalyzed 2,2,2‐trifluoroethoxyamination of olefins is developed via the formation corresponding alkoxy and iminyl radicals using unprecedented, easily prepared, bench‐stable oxime ethers as bifunctional reagents. To bypass possible side reactions (1,2‐Hydrogen Atom Transfer (HAT), H‐abstraction, β‐scission), high reactivity radical fine‐tuned to promote selective challenging a COCH 2 CF 3 bond. This reaction, involving triplet energy transfer process, allows concomitant CN COAlk bond, so far uncharted, ether Hence, difunctionalization myriad electron‐rich alkenes selectively afforded anti‐Markovnikov products with large functional group tolerance (44 examples, up 77% yield), offering straightforward complementary regioselectivity compared existing approaches for 2,2,2‐trifluoroethanol. Post‐functionalization mechanistic investigations provided key insights into reaction mechanism this transformation.

Язык: Английский

Energy Transfer Catalysis Enabled 2,2,2‐Trifluoroethoxy‐Amination of Olefins DOI Creative Commons
Floriane Doche, Thibault Gallavardin, Thomas Poisson

и другие.

ChemistryEurope, Год журнала: 2025, Номер unknown

Опубликована: Май 6, 2025

A thioxanthone‐catalyzed 2,2,2‐trifluoroethoxyamination of olefins is developed via the formation corresponding alkoxy and iminyl radicals using unprecedented, easily prepared, bench‐stable oxime ethers as bifunctional reagents. To bypass possible side reactions (1,2‐Hydrogen Atom Transfer (HAT), H‐abstraction, β‐scission), high reactivity radical fine‐tuned to promote selective challenging a COCH 2 CF 3 bond. This reaction, involving triplet energy transfer process, allows concomitant CN COAlk bond, so far uncharted, ether Hence, difunctionalization myriad electron‐rich alkenes selectively afforded anti‐Markovnikov products with large functional group tolerance (44 examples, up 77% yield), offering straightforward complementary regioselectivity compared existing approaches for 2,2,2‐trifluoroethanol. Post‐functionalization mechanistic investigations provided key insights into reaction mechanism this transformation.

Язык: Английский

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