Synthetic Strategies toward Ortho-3-propanoate Substituted Aryl Phosphonates by Three-Component Coupling Reactions of Arynes, Phosphites, and Acrylates DOI
Donghwa Shin, Soomin Kim, Duck‐Hyung Lee

и другие.

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

Recent Advances in the Application of P(III)-Nucleophiles to Create New P−C Bonds through Michaelis–Arbuzov-Type Rearrangement DOI
Biquan Xiong,

Minjing Yuan,

Chonghao Shi

и другие.

Topics in Current Chemistry, Год журнала: 2024, Номер 382(1)

Опубликована: Март 1, 2024

Язык: Английский

Процитировано

6

A simple method for N-arylation of secondary amides/amines through a NaH-initiated aryne generation strategy DOI

Yuanrui Jiang,

Wenjing Zhu,

Jiawen Huang

и другие.

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

The Reaction of Aryl Thiols or Thioureas with o‐Diiodoarenes/NaH to Access o‐Iodoaryl Thioethers DOI

Min Hu,

Dianfan Liu,

Yuan Liu

и другие.

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

Synthesis of Phosphachromones by Cyclized Coupling of Ethyl Hydrogen (Phenylethynyl)phosphonate with Arynes DOI
Yu Guo,

Jianke Su,

Jian Xu

и другие.

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

Recent Progress on Arylation with Aryne through Three-Component Reaction DOI Open Access
Dongping Chen,

Yang Chunhong,

Ming Li

и другие.

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 Aryne-Abramov Reaction as a 1,2-Benzdiyne Platform for the Generation and Solvent-Dependent Trapping of 3-Phosphonyl Benzynes DOI
Brianna M. Bembenek,

Maya M. S. Petersen,

Julia A. Lilly

и другие.

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

Synthesis of Benzoxaphosphole 1-Oxide Heterocycles via a Three-Component Coupling Reaction Involving Arynes, Phosphites, and Ketones DOI

Hee Jin Jeong,

Ji Ho Kim,

Jae Kyun Lee

и другие.

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

Fluoride-Mediated Aryne 1,2-Difunctionalization Involving C═S Bond Heterolysis DOI
Dong‐Ping Chen,

Chunhong Yang,

Wenpeng Wang

и другие.

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

Room-temperature synthesis of m-benzyne DOI
Kenta Koyamada, Kazunori Miyamoto, Masanobu Uchiyama

и другие.

Nature Synthesis, Год журнала: 2024, Номер 3(9), С. 1083 - 1090

Опубликована: Июль 17, 2024

Язык: Английский

Процитировано

1

Synthetic Strategy for Aryl(alkynyl)phosphinates by a Three-Component Coupling Reaction Involving Arynes, Phosphites, and Alkynes DOI

Su Hyun Ji,

Soomin Kim, Ghilsoo Nam

и другие.

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