Recent Advances in Trifluoromethylation of Olefins, Aldehydes, and Ketones

Current Organic Chemistry, Journal Year: 2024, Volume and Issue: 28(16), P. 1229 - 1243

Published: May 22, 2024

: Due to the robust electrophilic properties of trifluoromethyl group (-CF3), its incorporation into organic compounds can markedly alter their ester affinity, stability, bioavailability, and other properties. The trifluoromethylation reaction is currently experiencing rapid advancement, with an expanding array substrates emergence novel methodologies. Consequently, containing -CF3 moiety find extensive utility across diverse fields. This article aims comprehensively review latest advancements in olefins, aldehydes, ketones, encompassing nucleophilic trifluoromethylation, radical trifluoromethylation. discussion includes exploration types broadening scope applicable substrates. Furthermore, this addresses associated challenges delineates prospective directions for future developments reaction.

Language: Английский

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Efficient Trifluoromethylation of Halogenated Hydrocarbons Using Novel [(bpy)Cu(O2CCF2SO2F)2] Reagent

Molecules, Journal Year: 2024, Volume and Issue: 29(12), P. 2849 - 2849

Published: June 14, 2024

This study introduces a novel trifluoromethylating reagent, [(bpy)Cu(O2CCF2SO2F)2], notable for not only its practical synthesis from cost-effective starting materials and scalability but also nonhygroscopic nature. The reagent demonstrates high efficiency in facilitating trifluoromethylation reactions with various halogenated hydrocarbons, yielding products good yields exhibiting broad functional group compatibility. development of [(bpy)Cu(O2CCF2SO2F)2] represents an advancement the field organic synthesis, potentially serving as valuable addition to arsenal existing agents.

Language: Английский

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Synthesis of Fluorinated Spiroindolenines by Transition Metal‐Catalyzed Indole Dearomatizations

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(20), P. 4244 - 4252

Published: May 25, 2024

Abstract A strategy to access fluorinated spiroindolenines has been developed, involving a selective functionalization of indoles with moieties and subsequent catalytic dearomatization. Trifluomethylthio (SCF 3 ), diethyl phosphono(difluoromethyl)thio 2 P(O)(OEt) ) (phenylsulfonyl)difluoromethyl (CF SO Ph) groups were embedded at the C2 position indole derivatives substituted alkynes, allenes, allyl carbonate C3 position. gold‐catalyzed cycloisomerization gave five spiroindolenines, an enantioselective palladium catalyzed cyclization provided 10 spirocyclic products up 77% ee.

Language: Английский

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Visible-Light-Induced Cascade Radical Trifluoromethylation/Cyclization/Dearomatization of Isocyanide-Containing Indoles: Synthesis of Trifluoromethylated 3-Spiroindolines

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 4, 2024

A visible-light-induced cascade radical trifluoromethylation/cyclization/dearomatization reaction between isocyanide-containing indoles and CF3Br has been developed to afford trifluoromethylated spiro[indole-3,3-quinoline] spiro [indole-3,3-pyrrole] derivatives in good yields. The utility of the process is demonstrated by a scale-up experiment. mechanism was proposed based on control experiments. protocol constitutes novel efficient route for synthesis 3-spiroindolenines with advantages generality practical applicability, broad substrate scope, green energy source.

Language: Английский

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