The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown
Опубликована: Сен. 25, 2024
Carbene-catalyzed [3 + 3] annulation of enals and vinyl sulfoxonium ylides has been demonstrated. This method efficiently synthesizes a range 2-sulfenylidene-3-cyclohexen-1-ones with high atom economy. Notably, the presence ylide moiety in obtained products significantly enhances their potential for further synthetic transformations.
Язык: Английский
Advanced Science, Год журнала: 2025, Номер unknown
Опубликована: Апрель 2, 2025
Amide and alkene moieties are frequently found in natural products privileged structures pharmaceuticals agrochemicals. Moreover, vinyl sulfoxonium ylide can be converted into a broad range of high-value compounds, thus they have been widely employed organic synthesis. However, the synthesis alkene-substituted amide-sulfoxonium ylides via intermolecular hydrocarbonation alkynes remains underexplored. This study describes development high-throughput approach to provide diverse functionalized E-alkene substituted (hetero)amide-sulfoxonium ylides. The reaction occurs under mild metal-free conditions, employing as highly effective nucleophiles, which participate Michael addition reactions with various alkynes, such esters, thioesters, ketones, amides, sulfones. low-cost, operationally simple has substrate scope, high functional group compatibility, excellent regio- stereoselectivity, making it suitable for transformation structurally complex molecules. Furthermore, obtained stabilized directly useful valuable 1,5-dicarbonyl thiabenzene 1-oxide compounds.
Язык: Английский
Процитировано
0
Organic Letters, Год журнала: 2025, Номер unknown
Опубликована: Апрель 7, 2025
Here, we report a general and practical Doyle-Kirmse reaction of allyl/propargyl sulfides with donor-only vinyl carbenes generated in situ from triftosylhydrazones the presence silver catalyst. This protocol features mild conditions, exhibits broad substrate scope exceptional functional group tolerance, provides corresponding 1,5-dienyl 1,4-enallenyl high yields. Moreover, gram-scale synthesis, late-stage modifications complex molecules, post-synthetic transformations were performed to demonstrate applicability this protocol.
Язык: Английский
Процитировано
0
Organic Letters, Год журнала: 2024, Номер unknown
Опубликована: Сен. 17, 2024
A chiral-at-metal Rh(III) complex-mediated [2+1] cyclization of vinyl sulfoxonium ylides with α,β-unsaturated 2,2-acylimidazoles has been demonstrated for the first time. This work provides a practical approach assembling 1,2,3-trisubstituted chiral cyclopropane alkyl structural units, which had advantages such as wide range substrates, good functional group tolerance, and mild reaction conditions. In addition, further amplification experiments transformation cycloaddition products were carried out to highlight practicality method.
Язык: Английский
Процитировано
2
Synthesis, Год журнала: 2024, Номер unknown
Опубликована: Июнь 21, 2024
Abstract A visible-light-induced multicomponent reaction of vinyl sulfoxonium ylide, thiol, and diazo ester to generate tertiary sulfide is described. The present diastereoselective gem-difunctionalization the can be achieved under mild conditions, as it does not require any additives, catalysts, or transition metals tolerant air moisture. Due more nucleophilicity, ylide undergoes S–H insertion with thiols an allyl intermediate. Simultaneously, photolysis a carbene Subsequently, coupling intermediates generates sulfonium which Doyle–Kirmse rearrangement scaffolds.
Язык: Английский
Процитировано
0
Organic Letters, Год журнала: 2024, Номер 26(26), С. 5566 - 5570
Опубликована: Июнь 21, 2024
We disclose an efficient nickel catalytic system for expediting the coupling of alkynes with fluoroalkyl hydrazones and boronic acids, thus facilitating synthesis stereospecific α-fluoroalkyl-alkene derivatives. 3H-Pyrazoles might be involved as key intermediates through a nitrogen-releasing process, enabling subsequent acids to afford 1,2-difunctional alkenes in highly step-economical fashion. This tandem platform demonstrates broad functional group tolerance, including complex natural products drug-like molecules.
Язык: Английский
Процитировано
0
The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown
Опубликована: Сен. 25, 2024
Carbene-catalyzed [3 + 3] annulation of enals and vinyl sulfoxonium ylides has been demonstrated. This method efficiently synthesizes a range 2-sulfenylidene-3-cyclohexen-1-ones with high atom economy. Notably, the presence ylide moiety in obtained products significantly enhances their potential for further synthetic transformations.
Язык: Английский
Процитировано
0