HFIP-Mediated, Regio-, and Stereoselective Hydrosulfenylation of Ynamides: A Versatile Strategy to Access Ketene N,S-Acetals

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Herein, we report an HFIP-mediated, versatile, sustainable, atom-economical, and regio- stereoselective hydro-functionalization of ynamides with various S-nucleophiles (1 equiv.) such as thiols, thiocarboxylic acids, carbamates, xanthates, O,O-diethyl S-hydrogen phosphorothioate to access a wide variety stereodefined trisubstituted ketene N,S-acetals under mild conditions. This protocol requires only HFIP, which plays multiple roles, acting Brønsted acid protonate the ynamide regioselectively at beta carbon generate reactive keteniminium intermediate, stabilizing intermediate solvent through H-bonding. After nucleophilic attack S-nucleophile on deprotonation, HFIP is regenerated in most cases can be easily recovered recycled, revealing high sustainability protocol. Remarkably, all reactions are highly efficient furnish excellent yields many pure products were obtained just by washing crude reaction mixture pentane. Significantly, green chemistry metrics found excellent.

Language: Английский

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Synthesis of 2-Organoselenyl Quinolines via Electro-Oxidative Selenocyclization of Isocyanides

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 12, 2025

Organoselenium compounds and quinolines are widely used in drugs materials. Herein, we report an electro-oxidative cyclization between isocyanides diselenides to effectively synthesize 2-organoselenyl a simple undivided cell without transition-metal catalysts or toxic oxidants. Gram-scale synthesis postsynthetic modifications highlighted the practicality of this electrochemical strategy. A series produced with up 82% yield, good functional group tolerance high atom efficiency under room temperature.

Language: Английский

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Electrochemically Chalcogenative Annulation Enabled Construction of Functionalized Saturated N-Heterocycles†

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(74), P. 10156 - 10159

Published: Jan. 1, 2024

An efficient chalcogenative annulation strategy for constructing functionalized saturated N-heterocycles from unactivated alkenes with dichalcogenides under electrochemical conditions has been presented. This protocol is applicable to mono-, di- or tri-substituted alkenes, providing a straightforward pathway aziridines, azetidines, pyrrolidines, and piperidines high regioselectivity. Moreover, the qualified realize oxychalcogenation of as well.

Language: Английский

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Electrochemically promoted selenocyclization for the synthesis of organoselenyl isoxazoles

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(19), P. 10240 - 10246

Published: Jan. 1, 2024

Herein, we report a general and sustainable electrochemically promoted oxidative selenocyclization protocol for the synthesis of organoselenyl isoxazoles from 2-alkyn-1-one O -methyloximes diorganyl diselenides.

Language: Английский

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Visible-Light-Mediated, Organophotocatalytic C–H Thiocyanation of Pyrazolo[1,5-a]pyrimidines

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13215 - 13223

Published: Sept. 11, 2024

Herein, we report a metal-free, organophotoredox-catalyzed sustainable C-H thiocyanation of biologically active class N-heterocycles, pyrazolo[1,5-

Language: Английский

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