Visible-Light-Induced photoredox aerobic coupling of sulfonium ylides and amines leading to E-selective formation of 2-amino-2-butene-1,4-diones

Organic Chemistry Frontiers, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A novel visible-light-induced photoredox three-component aerobic coupling reaction of sulfoxonium ylides and amines is reported.

Language: Английский

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Asymmetric synthesis of spirofuro[2,3-b]azepine-5,3′-indoline derivativesviacycloisomerization/[4 + 3] annulation process under Au/N-heterocyclic carbene relay catalysis

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(13), P. 3347 - 3352

Published: Jan. 1, 2023

A variety of enantioenriched spirofuro[2,3- b ]azepine-5,3’-indoline derivatives were synthesized via Au(I)/chiral NHC relay catalyzed cycloisomerization/asymmetric [4+3] annulation.

Language: Английский

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Synthesis of S-alkyl phosphorothioates/phosphorodithioates via ring-opening reaction of sulfonium salts with S₈, H-phosphonates or P₄S₁₀, and alcohols

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(20), P. 5731 - 5740

Published: Jan. 1, 2024

A simple and practical method for the synthesis of S -alkyl phosphorothioates/phosphorodithioates through three-component reaction cyclic sulfonium salts with 8 , H -phosphonates, or P 4 10 alcohols was readily developed.

Language: Английский

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Lewis Acid Promoted Vicinal Oxytrifluoromethylselenolation of Alkenes

Organic Letters, Journal Year: 2023, Volume and Issue: 25(18), P. 3210 - 3215

Published: April 28, 2023

Herein, we have developed a metal-free, Lewis acid promoted vicinal oxytrifluoromethylselenolation of alkenes using trifluoromethyl selenoxides as electrophilic trifluoromethylselenolation reagents and alcohols nucleophiles. With less steric good nucleophilic solvents (such ethanol methol), Tf2O-catalyzed could be realized, while stoichiometric Tf2O was required to promote full transformation with isopropanol tert-butanol). The reaction featured substrate scope, functional group compatibility, diastereoselectivity. This method further applied oxytrifluoromethylselenolation, aminotrifluoromethylselenolation nucleophiles under modified conditions. A mechanism involving seleniranium ion proposed based on the preliminary results.

Language: Английский

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Visible-Light-Induced Monofluoroalkenylation and gem-Difluoroallylation of Inactivated C(sp³)–H Bonds via 1,5-Hydrogen Atom Transfer (HAT)

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(6), P. 3883 - 3896

Published: March 7, 2023

The direct monofluoroalkenylation of C(sp3)–H bonds is great importance and quite challenging. Current methods have been restricted to the activated bonds. Here, we reported photocatalyzed inactivated with gem-difluoroalkenes via 1,5-hydrogen atom transfer. This process shows good functional group tolerance, such as halides (F, Cl), nitrile, sulfone, ester, pyridine, γ-selectivity. Moreover, this method succeeds in gem-difluoroallylation α-trifluoromethyl alkenes.

Language: Английский

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Recent Advances in Domino Synthesis of Fused Polycyclic N‐Heterocycles Based on Intramolecular Alkyne Hydroamination under Copper Catalysis

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 41(24), P. 3751 - 3771

Published: Sept. 4, 2023

Comprehensive Summary Fused polycyclic N ‐heterocycles are very important scaffolds in biomedicinal chemistry and materials science. Intramolecular alkyne hydroamination is a powerful method for the construction of ‐heterocycles. In last two decades, copper‐catalyzed domino reactions based on intramolecular has emerged as robust strategy assembling various fused Great progress been achieved this area. This short review covers advances made synthesis from 2008 to 2023, will hopefully serve an inspiration towards exploration new versions transformation. The transformations introduced discussed five aspects according different key processes involved these reactions.

Language: Английский

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Ring expansion of spirocyclopropanes with stabilized sulfonium ylides: highly diastereoselective synthesis of cyclobutanes

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(34), P. 4537 - 4540

Published: Jan. 1, 2024

A novel method was devised for regioselective ring expansion of spirocyclopropanes to spirocyclobutanes with stabilized sulfonium ylides, affording 1,2- trans -disubstituted 6,8-dioxaspiro[3.5]nonane-5,9-diones without the formation any isomers.

Language: Английский

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Brønsted Acid‐Assisted Lewis Acid Mediated Intramolecular Trapping of Aminoenol with Activated Alkenes and Ketones

Chemistry - An Asian Journal, Journal Year: 2025, Volume and Issue: unknown

Published: April 14, 2025

Abstract An efficient Brønsted acid‐assisted Lewis acid‐mediated synthesis of indolines and pyrrolidines has been achieved from α‐hydroxydimethylacetals suitable electrophile‐tethered amines. The reaction proceeds via an interrupted Amadori/Heyns rearrangement, where the key aminoenol intermediate was successfully trapped with Michael acceptors ketones in intramolecular fashion to afford corresponding derivatives good yield diastereoselectivity. is operationally simple, general, tolerates various functional groups.

Language: Английский

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Applications of Sulfur Ylide-Mediated Specific Reaction Types in Heterocyclic Synthesis

Advances in Material Chemistry, Journal Year: 2025, Volume and Issue: 13(02), P. 225 - 235

Published: Jan. 1, 2025

Language: Английский

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NHC-catalyzed [12+2] reaction of polycyclic arylaldehydes for access to indole derivatives

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(42), P. 6351 - 6354

Published: Jan. 1, 2023

An N-heterocyclic carbene (NHC) catalyzed enantio- and diastereoselective [12+2] cycloaddition is disclosed to rapidly construct sophisticated molecules bearing a tricyclic core morpholine moiety. The success of our reaction relies on the NHC-catalyzed remote sp3 (C-H) bond activation 5H-benzo[a]pyrrolizine-3-carbaldehyde under oxidative conditions. Preliminary studies revealed that products exhibit superior in vitro bioactivities against two plant pathogens commercial Bismerthiazol (BT) Thiodiazole Copper (TC).

Language: Английский

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