Sulfoximine Assisted C–H Activation and Annulation via Vinylene Transfer: Access to Unsubstituted Benzothiazines DOI Creative Commons
Koneti Kondalarao, Somratan Sau, Akhila K. Sahoo

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(13), P. 5014 - 5014

Published: June 27, 2023

In this study, we report the synthesis of unsubstituted 1,2-benzothiazines through a redox-neutral Rh(III)-catalyzed C–H activation and [4+2]-annulation S–aryl sulfoximines with vinylene carbonate. Notably, introduction an N-protected amino acid ligand significantly enhances reaction rate. The key aspect process is utilization carbonate as oxidizing acetylene surrogate efficient transfer agent. This enables cyclization sulfoximine motifs, successfully forming diverse array 1,2-benzothiazine derivatives in moderate to good yields. Importantly, study highlights potential reactions for optically pure high enantiomeric purity.

Language: Английский

Construction of Ultrastable Nonsubstituted Quinoline‐Bridged Covalent Organic Frameworks via Rhodium‐Catalyzed Dehydrogenative Annulation DOI
Xiaodong Zhao,

Huaji Pang,

Dekang Huang

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(41)

Published: Aug. 24, 2022

Exploring new routes to lock the dynamic C=N bonds in imine-linked covalent organic frameworks (COFs) is highly desired for enhancing their stability and functionality. Herein, a novel bridge locking strategy via rhodium-catalyzed [4+2] annulation developed construct nonsubstituted quinoline-linked COFs (NQ-COFs). The notable feature of this includes high conversion efficiency, oxidant-free, generality synthesis variety NQ-COFs with chemical stability. Particularly, after post-synthetic modification, crystallinity, topology, porosity pristine are well retained. When used as photocatalysts, display better visible light absorption carriers' separation efficiency due enhanced in-plane π conjugation ability, more facile generation superoxide anion radicals than counterparts, thus leading efficient 2,4,6-tris(aryl)pyridines, benzimidazole, sulfoxide derivatives.

Language: Английский

Citations

50
Photo-Thermo-Mechanochemical Approach to Synthesize Quinolines via Addition/Cyclization of Sulfoxonium Ylides with 2-Vinylanilines Catalyzed by Iron(II) Phthalocyanine DOI
Luyao Liu,

Jingyang Lin,

Mingxuan Pang

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(5), P. 1146 - 1151

Published: Feb. 3, 2022

A novel photo-thermo-mechanochemical approach to assembling quinolines catalyzed by iron(II) phthalocyanine has been realized for the first time. This transformation features a cost-efficient catalytic system and operational simplicity, is free of solvent, shows good substrate tolerance, providing green alternative existing thermal approaches. Mechanistic experiments demonstrate that in-situ-formed secondary amine may be key intermediate further cyclization/aromatization process.

Language: Английский

Citations

29
Rh(III)-Catalyzed Synthesis of Indazolo[2,3-a]quinolines: Vinylene Carbonate as C1 and C2 Building Blocks DOI
Wei Hu, Chao Pi, Di Hu

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(14), P. 2613 - 2618

Published: April 4, 2022

A rhodium-catalyzed cyclization of azobenzenes and vinylene carbonate via C-H bond activation to construct indazolo[2,3-a]quinolines has been developed. This protocol offers an efficient method for synthesis the titled products in good yields with broad functional group tolerance. In this reaction, three C-C bonds C-N are formed one pot, (VC) acts as C1 C2 synthons well "vinylene transfer" agent acylation reagent construction target-fused heterocycles. Moreover, exhibit favorable fluorescence properties, which indicate their potential application fluorescent materials biosensors.

Language: Английский

Citations

28
Selective Synthesis of C4-Functionalized Benzofurans by Rhodium-Catalyzed Vinylene Transfer: Computational Study on the Cyclopentadienyl Ligand DOI

Junya Kitano,

Yuji Nishii, Masahiro Miura

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(31), P. 5679 - 5683

Published: July 28, 2022

Benzofuran is a privileged structure in many bioactive compounds; however, the controlled synthesis of C2,C3-nonsubstituted benzofurans has been scarce. In particular, cumbersome multistep processes are inevitable for most inaccessible C4-substituted isomers. Herein, we report Rh-catalyzed direct vinylene annulation readily available m-salicylic acid derivatives with carbonate to achieve selective construction benzofurans. The Weinreb amide directing group facilitated following product derivatization. reaction mechanism was investigated by DFT calculations.

Language: Английский

Citations

26
Ruthenium-catalyzed oxidative coupling of vinylene carbonate with isoxazoles: access to fused anthranils DOI
Pravin Kumar, Manmohan Kapur

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(28), P. 4476 - 4479

Published: Jan. 1, 2022

A ruthenium-catalyzed oxidative coupling of vinylene carbonate with isoxazoles has been developed to achieve the direct C-H formylmethylation a diverse array arylisoxazoles utilizing isoxazole ring as directing group. simple manipulation established reaction conditions leads formation fused-anthranils. Importantly, functions both formylmethyl cation equivalent through decarboxylation process and an acetylene equivalent. Control experiments were conducted elucidate plausible mechanism. This methodology is expected provide facile expeditious approach for synthesis

Language: Английский

Citations

25
Advancement of vinylene carbonate as a coupling partner in metal-catalyzed C–H functionalization DOI

Yicong Ge,

Qiang Yan,

Jiang Nan

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(22), P. 5717 - 5734

Published: Jan. 1, 2023

Vinylene carbonate (VC) has emerged as a promising coupling partner to participate in various attractive C–H conversions and implement an increasing number of novel reactions. In this review, we provide summary the advancements achieved metal-catalyzed functionalization using VC.

Language: Английский

Citations

16
Rhodium‐Catalyzed Direct Vinylene Annulation of Sulfoxonium Ylides and N‐carbamoylindoles with Vinylene Carbonate DOI

Jia‐Lin Song,

Lin Xiao,

Shaoyong Chen

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(9), P. 1457 - 1464

Published: April 14, 2023

Abstract In this study, Rh(III)‐catalyzed C−H bifunctionalization and direct vinylene annulation of sulfoxonium ylides N ‐carbamoylindoles with carbonate was accomplished, which afforded a series naphthalenones containing β‐ketosulfoxonium ylide moiety, isocoumarins, pyrimidones. This protocol featured mild conditions, broad substrate scope, functional‐groups compatibility. addition, related applications preliminary mechanistic exploratory were also investigated magnified image

Language: Английский

Citations

14
Three-Component Synthesis of 2-Substituted Quinolines and Benzo[f]quinolines Using Tertiary Amines as the Vinyl Source DOI
Yanfeng Ma,

Chunlan Zhou,

Fuhong Xiao

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(5), P. 2952 - 2960

Published: Feb. 20, 2023

A metal-free method for the construction of 2-substituted quinolines and benzo[f]quinolines from aromatic amines, aldehydes, tertiary amines has been demonstrated. Cheap readily available acted as vinyl source. new pyridine ring was selectively formed via [4 + 2] condensation that promoted by ammonium salt under neutral conditions an oxygen atmosphere. This strategy provided a route preparation various quinoline derivatives with different substituents at ring, which provides possibility further modification.

Language: Английский

Citations

13
Chemical upcycling of poly(bisphenol A carbonate) to vinylene carbonates through organocatalysis DOI Creative Commons
Killian Onida,

Mohamad Fayad,

Sébastien Norsic

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(11), P. 4282 - 4291

Published: Jan. 1, 2023

The chemical upcycling of poly(bisphenol A carbonate) was carried out through organocatalysis using α-hydroxyketones as nucleophiles, leading to valuable vinylene carbonates.

Language: Английский

Citations

11
Vinylene Carbonate as Synthon in Transition Metal‐Catalyzed C−H Bond Activation/Annulation Reactions DOI Open Access

Xiaofan Cui,

Rémi Chauvin, Chao Pi

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(20), P. 3400 - 3412

Published: Sept. 6, 2023

Abstract Recently, vinylene carbonate has been developed as a powerful synthon in transition metal‐catalyzed C−H bond activation/cyclization reactions. This review introduces recent progress the use of reactant, by analyzing and comparing reaction models involving surrogate ethynol, acetylene, acetylation reagents or other reactants, while addressing related mechanisms synthetic applications.

Language: Английский

Citations

11