Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(11), С. 1903 - 1907
Опубликована: Апрель 21, 2022
Abstract 5‐Oxazoyl‐sulfamates have been profiled as versatile building blocks for modifications of oxazoles with various nucleophiles. The unified approach provides a diversification platform to directly access 5‐amino‐oxazoles, 5‐oxazolyl‐sulfides, and 5‐oxazoyl‐aryl ethers from single precursor. magnified image
Язык: Английский
Green Chemistry, Год журнала: 2022, Номер 24(8), С. 3314 - 3320
Опубликована: Янв. 1, 2022
Gold( i )-catalyzed highly regioselective hydration of alkynylsulfones comprises an efficient 100% atom-economic route to β-ketosulfones.
Язык: Английский
Процитировано
24
Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(19), С. 5133 - 5140
Опубликована: Янв. 1, 2022
The developed modular approach to hard-to-reach non-aromatic 3 H - and 2 -pyrroles is based on the integration of -azirines ynamides.
Язык: Английский
Процитировано
22
Journal of the American Chemical Society, Год журнала: 2022, Номер 144(18), С. 8306 - 8316
Опубликована: Апрель 26, 2022
New N-heterocyclic fluorophores are sought-after compounds for organic electronic devices. Here, we report on a straightforward synthesis to access meta/para-dipyrrolobenzenes and para-dipyrrolopyrazines in high yields using bidirectional gold-catalyzed cyclization strategy. The versatility of our reaction protocol was showcased by preparing dipyrroloarenes with different substituents, various functional groups, multitude substitution patterns. Furthermore, showed that the can be post-modified N-alkylation improve solubility or bromination yield precursors further derivatization via cross-coupling. Investigation photophysical properties the─mostly unprecedented─dipyrroloarenes identified strong blue emitters such as diphenyl meta-dipyrrolobenzene quantum 98%. Moreover, changes solvent polarity interactions Lewis acids borane used fine-tune fluorophores.
Язык: Английский
Процитировано
21
Organic Letters, Год журнала: 2024, Номер 26(3), С. 631 - 635
Опубликована: Янв. 12, 2024
A gold-catalyzed, nucleophile-controlled cascade reaction of N-(2-azidophenyl-ynyl)methanesulfonamides with nitriles and water is described that provides structurally diverse 5H-pyrimido[5,4-b]indoles 2-benzylidene-3-indolinones in good to excellent yields. Mechanistic studies indicate the β-sulfonamido-α-imino gold carbene key intermediate which generated through gold-catalyzed cyclization undergoes formal [4 + 2] annulation intramolecular SN2′ type water, respectively.
Язык: Английский
Процитировано
5
Tetrahedron, Год журнала: 2025, Номер unknown, С. 134484 - 134484
Опубликована: Янв. 1, 2025
Язык: Английский
Процитировано
0
Organic Letters, Год журнала: 2025, Номер unknown
Опубликована: Март 24, 2025
We report on gold-catalyzed oxygen transfer utilizing, for the first time, electron-deficient trifluoromethylated alkynes as substrates. This double O-transfer process provides a direct and convenient one-step route to difficult-to-obtain 1,2-diketones. Due relatively mild oxidative reaction conditions (rt 60 °C, 2,6-dichloropyridine N-oxide an oxidizer, 3 mol % JohnPhosAuNTf2), various functional substituents were tolerated (19 examples; yields up 95%). The synthetic utility of obtained dicarbonyl products was further explored, these studies included one-pot multicomponent syntheses valuable CF3-substituted indoles benzofurans.
Язык: Английский
Процитировано
0
Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(21), С. 3697 - 3707
Опубликована: Сен. 24, 2022
Abstract The gold‐catalyzed annulation of alkynylsulfones, involving pyridine N ‐oxides (as O ‐atom transfer reagents) and nitriles C=N synthons), comprises a diazo‐free route to valuable 4‐sulfonyl‐1,3‐oxazoles. This reaction operates under relatively mild conditions (IPrAuNTf 2 5 mol %, rt or 60 °C), number functionalities was compatible (35 examples; 14–95%). In most cases, the SO fragment, which is typically expulsed in previously reported Au‐catalyzed ‐transfers retains heterocyclic products. postulated mechanism suggests key role reactive gold α‐oxo carbene intermediates formed via transfer. magnified image
Язык: Английский
Процитировано
14
The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(9), С. 5882 - 5892
Опубликована: Апрель 12, 2022
A tandem addition/cyclization reaction between trifluoromethyl N-acylhydrazones and cyanamide is described, which provides a novel efficient process for the synthesis of polysubstituted 3-trifluoromethyl-1,2,4-triazolines their derivatives. The method has advantages mild conditions, broad substrate scope, good product yields, atom economy.
Язык: Английский
Процитировано
13
Chemistry - A European Journal, Год журнала: 2023, Номер 29(70)
Опубликована: Сен. 28, 2023
Abstract Gold catalysis is an important method for alkyne functionalization. Here we report the gold‐catalyzed formal [3+2] aminative cyclization of yndiamides and isoxazoles in a direct synthesis polysubstituted diaminopyrroles, which are motifs drug discovery. Key to this process formation, subsequent cyclization, α‐imino gold Fischer carbene, represents new type carbene intermediate. The reaction proceeds rapidly under mild conditions, with high regioselectivity being achieved by introducing subtle steric bias between nitrogen substituents on yndiamide. DFT calculations revealed that key was interconversion isomeric keteniminiun ions via low‐barrier π‐complex transition state, establishes Curtin‐Hammett scenario isoxazole addition. By using benzisoxazoles as substrates, outcome could be switched [5+2] leading 1,4‐oxazepines.
Язык: Английский
Процитировано
8
Tetrahedron, Год журнала: 2021, Номер 102, С. 132544 - 132544
Опубликована: Ноя. 6, 2021
Язык: Английский
Процитировано
18