Pentafluorosulfanoxylation of Hypervalent Chlorines and Bromines for Access to Pentafluoro(biaryloxy)-λ⁶-sulfanes

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 11, 2025

The SF5O group has been less explored as a highly fluorinated substituent on an organic framework. In fact, only few SF5O-containing compounds have reported, and the preparation of relied hazardous reagents special apparatuses. Herein we describe safe efficient access to various pentafluoro(aryloxy)-λ6-sulfanes (ArOSF5) through reaction hypervalent λ3-chlor(brom)anes with [Et3MeN]+[OSF5]−. synthetic application potentials ArOSF5 moieties were demonstrated by inertness OSF5 in presence palladium catalysts, alkalis, nucleophiles.

Язык: Английский

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Synthesis of α-SF₅ Ketones by Oxypentafluorosulfanylation of Alkynes with SF₅Cl and Oxygen

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 18, 2025

Herein for the first time, we disclose a practical and straightforward approach to access α-SF5 ketones via direct oxypentafluorosulfanylation of alkynes with SF5Cl oxygen under acidic conditions by one step. The protocol features mild reaction conditions, broad substrate scope, good functional group compatibility can be applied late-state functionalization complex natural products pharmaceuticals. A radical mechanism involving SF5 addition triple bonds followed O2 capture is proposed.

Язык: Английский

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Substrate-Controlled Pentafluorosulfanylation of Activated Alkenes Containing the Benzimidazole Moiety with SF₅Cl

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 14, 2025

We report herein a method of substrate-controlled pentafluorosulfanylation activated alkenes containing the benzimidazole moiety with SF5Cl, which provides highly efficient way to access SF5-containing benzo[4,5]imidazole[2,1-a]isoquinolin-6(5H)-ones, as well N-benzoyl benzimidazoles. Besides pentafluorosulfanyl group (-SF5), current can be applied tetrafluorosulfanyl (-SF4-) incorporation. A radical mechanism involving single electron transfer (SET) or atom addition (ATRA) process is proposed.

Язык: Английский

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Fluorohydrins and where to find them: recent asymmetric syntheses of β-fluoro alcohols and their derivatives

Organic & Biomolecular Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

The present work provides an overview of synthetic approaches to fluorohydrins and their fluorinated group derivatives that have been explored in the past decade, as well selected examples these syntheses applied medicinal chemistry.

Язык: Английский

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Exploration of 2-(pentafluoro-λ6-sulfanyl)ethane-1-sulfonyl chloride as a novel pentafluorosulfanylation reagent.

Journal of Fluorine Chemistry, Год журнала: 2024, Номер unknown, С. 110387 - 110387

Опубликована: Дек. 1, 2024

Язык: Английский

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Exploration towards the bromopentafluorosulfanylation reaction of terminal alkynes

Journal of Fluorine Chemistry, Год журнала: 2024, Номер unknown, С. 110386 - 110386

Опубликована: Дек. 1, 2024

Язык: Английский

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