The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(11), С. 8035 - 8040
Опубликована: Май 28, 2024
Mild, metal-free, and operationally simple three-component coupling reactions involving arynes, phosphites, acrylates have been achieved. The reaction proceeded well with α- or β-substituted acrylates. Additionally, various functional groups were tolerated under these conditions, resulting in diverse
Язык: Английский
Topics in Current Chemistry, Год журнала: 2024, Номер 382(1)
Опубликована: Март 1, 2024
Язык: Английский
Процитировано
6
Organic Chemistry Frontiers, Год журнала: 2023, Номер 11(1), С. 12 - 20
Опубликована: Окт. 3, 2023
A very simple and practical method has been uncovered for N -arylation of many sets secondary amides/amines.
Язык: Английский
Процитировано
10
Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(7), С. 1538 - 1544
Опубликована: Фев. 8, 2024
Abstract Herein we report a method for the synthesis of thioethers by forging C(aryl)‐S bond via an aryne mechanism. The active species can be generated from o ‐diiodoarenes and NaH in THF at room temperature, then lead to arylations wide range aryl thiols thioureas. Different transition metal‐catalyzed cross‐coupling reactions, no disubstituted byproduct is formed our protocol. ‐iodoaryl thioether products are intermediates that could transformed into pharmaceutically interesting molecules.
Язык: Английский
Процитировано
4
Organic Letters, Год журнала: 2023, Номер 25(35), С. 6459 - 6463
Опубликована: Авг. 25, 2023
A straightforward and efficient strategy for the synthesis of phosphachromones has been reported via insertion arynes into P–O bonds. This operationally simple reaction is compatible with different functional groups, affording various by simultaneous formation C–P C–O bonds in one step moderate to good yields, Fries rearrangement involving phosphorus atoms a key reaction.
Язык: Английский
Процитировано
6
Chinese Journal of Organic Chemistry, Год журнала: 2023, Номер 43(2), С. 503 - 503
Опубликована: Янв. 1, 2023
The three component reaction has the advantages of simple operation and efficient reaction, in line with principles atomic economy green environmental protection.At present, arylation without transition metal catalyst is mainly divided into types as following: (1) direct arylation, (2) insertion aryne σ-bond or π-bond, (3) three-component reactions involving aryne.Compared mechanism still unclear, published reviews are lacking.In order to facilitate scientific researchers consult understand involved aryne, progresses recent years reviewed.
Язык: Английский
Процитировано
5
The Journal of Organic Chemistry, Год журнала: 2021, Номер 86(15), С. 10724 - 10746
Опубликована: Июль 8, 2021
Synthetic methodology utilizing two aryne intermediates (i.e., a formal benzdiyne) enables the rapid generation of structurally complex molecules with diverse functionality. This report describes sequential ortho-benzyne for synthesis 2,3-disubstituted aryl phosphonates. Aryl phosphonates have proven useful in medicinal chemistry and materials science, reported provides two-step route to functionally dense variants by way 3-phosphonyl benzyne intermediates. The process begins regioselective trapping 3-trifloxybenzyne intermediate an O-silyl phosphite Abramov-like reaction bond strained Csp carbons phosphorus silicon. Standard aryne-generating conditions follow convert resulting 2-silylphenyl triflate into benzyne, which readily reacts numerous reactants form variety 2,3-difunctionalized phosphonate products. DFT computational studies shed light on important mechanistic details revealed that benzynes are highly polarizable. Specifically, distortion internal angles at each atoms was strongly influenced both electronegativity ester groups as well dielectric solvation model. These effects were verified experimentally regioselectivity benzyl azide increased more electronegative esters and/or increasingly polar solvents. Conversely, replacing conventional solvent, acetonitrile, nonpolar alternatives provided attenuated or even inverted selectivities. Overall, these showcase new reactivity extend relay include organophosphonates. Furthermore, this work demonstrates reactions could be tuned simply changing solvent.
Язык: Английский
Процитировано
11
Organic Letters, Год журнала: 2022, Номер 24(11), С. 2192 - 2196
Опубликована: Март 14, 2022
An efficient and transition-metal-free three-component reaction with benzynes formed in situ from 2-(trimethylsilyl)aryl triflate, phosphites, ketones was developed for the synthesis of benzoxaphosphole 1-oxides. array 1-oxides were prepared both activated non-activated moderate to good yields a broad functional group tolerance. This is useful preparing organophosphorus compounds encountered natural products materials.
Язык: Английский
Процитировано
8
The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown
Опубликована: Июль 1, 2024
We have successfully synthesized a series of bidentate ligands by utilizing 2-(trimethylsilyl)phenyl trifluorosulfonate as precursor for the benzyl group. This method proceeded inserting polythiourea into C═S π-bond, intramolecular ring proton migration, and opening. Salient features this strategy are mild reaction conditions, novel product structure, excellent stereochemistry, good functional group tolerance. Furthermore, density theory calculations were performed to gain insights transfer mechanism.
Язык: Английский
Процитировано
1
Nature Synthesis, Год журнала: 2024, Номер 3(9), С. 1083 - 1090
Опубликована: Июль 17, 2024
Язык: Английский
Процитировано
1
Organic Letters, Год журнала: 2022, Номер 24(45), С. 8295 - 8299
Опубликована: Ноя. 7, 2022
An efficient and straightforward method for the synthesis of aryl(alkynyl)phosphinates was developed via a three-component coupling reaction involving arynes, phosphites, alkynes. array were produced from both aryl aliphatic group-substituted acetylenes. This operationally simple is tolerant to many functional groups, affording various in moderate good yields. The synthetic utility alkynyl phosphinates afforded by this demonstrated elaboration products into phosphorus-containing compounds.
Язык: Английский
Процитировано
6