Synthesis of 1‐Aminoisoquinolines and Their Application in a Host‐Guest Doped Strategy To Construct Ultralong Room‐Temperature Phosphorescence Materials for Bioimaging DOI

Lepeng Chen,

Wenzhang Xiong,

Yaogeng Ma

et al.

Chemistry - A European Journal, Journal Year: 2022, Volume and Issue: 29(5)

Published: Nov. 3, 2022

Organic ultralong room-temperature phosphorescence (RTP) materials have attracted great attention for their wide applications in optoelectronic devices and bioimaging. However, the development of these remains a challenging task, partially due to lack rational molecular design strategies unclear luminescence mechanisms. Herein, we present method facile access structurally diverse substituted 1-aminoisoquinoline derivatives through copper-catalyzed one-pot three-component coupling reaction that provides promising approach rapidly assemble library 1-aminoisoquinolines exploring regularity host-guest doped system. A series RTP with wide-ranging lifetimes from 4.4 299.3 ms were constructed by doping various isoquinolines into benzophenone (BP). Furthermore, 4 r/BP nanoparticles could be used in-vivo imaging signal-to-noise ratio value as high 32, revealing potential isoquinoline framework construction high-performance materials.

Language: Английский

Rhodium-Catalyzed Dehydrogenative Annulation of N-Arylmethanimines with Vinylene Carbonate for Synthesizing Quinolines DOI
Yan Hu, Jiang Nan,

Jiacheng Yin

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(21), P. 8527 - 8532

Published: Oct. 20, 2021

Here we report a novel Rh-catalyzed C−H/C−H alkenylation of N-arylmethanimines with vinylene carbonate acting as unit. Forty examples C3,C4-nonsubstituted quinolines were achieved from commercially available starting materials. This identified process features an exceedingly simple system, lower loading catalyst, and the capacity for postfunctionalization bioactive molecules.

Language: Английский

Citations

46

Rhodium-catalysed direct formylmethylation using vinylene carbonate and sequential dehydrogenative esterification DOI

Moena Kato,

Koushik Ghosh, Yuji Nishii

et al.

Chemical Communications, Journal Year: 2021, Volume and Issue: 57(67), P. 8280 - 8283

Published: Jan. 1, 2021

A rhodium-catalysed direct formylmethylation adopting vinylene carbonate as an ethynol equivalent is reported.

Language: Английский

Citations

37

Manganese-Catalyzed [4 + 2] Annulation of N–H Amidines with Vinylene Carbonate via C–H Activation DOI
Yudong Li, Huan Wang, Ying Li

et al.

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(24), P. 18204 - 18210

Published: Nov. 25, 2021

Manganese-catalyzed C-H bond functionalization of aryl amidines for the synthesis 1-aminoisoquinolines in presence vinylene carbonate has been developed. The reaction features a broad substrate scope and proceeds under mild conditions with only anion as byproduct.

Language: Английский

Citations

33

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

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

Rhodium-Catalyzed C–H Annulation of Free Anilines with Vinylene Carbonate as a Bifunctional Synthon DOI
Jiang Nan,

Jiacheng Yin,

Xue Gong

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(22), P. 8910 - 8915

Published: Nov. 10, 2021

Chemical transformation with vinylene carbonate as an emerging synthetic unit has recently attracted considerable attention. This report is a novel conversion pattern carbonate, in which such vibrant reagent unprecedentedly acts difunctional coupling partner to complete the C-H annulation of free anilines. From commercially available substrates, this protocol leads rapid construction synthetically versatile 2-methylquinoline derivatives (43 examples) excellent functionality tolerance.

Language: Английский

Citations

31

Rhodium-Catalyzed Isoquinoline Synthesis Using Vinyl Selenone as Oxidizing Acetylene Surrogate DOI

Ayumi Inami,

Yuji Nishii, Koji Hirano

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(18), P. 3206 - 3209

Published: May 4, 2023

Isoquinoline is a privileged structure in many bioactive compounds and valuable ligands. Transition-metal-catalyzed oxidative annulation of imine derivatives has become promising synthetic method; however, catalytic synthesis 3,4-nonsubstituted isoquinolines by formal acetylene been scarce to date. Herein, we introduce vinyl selenone as an effective surrogate for the Rh-catalyzed annulative coupling under mild conditions. The Se fragment can be recovered diselenide recycled. product readily converted 1-aminoisoquinolines.

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

Transition metal-free annulative vinylene transfer via the 1,3-dipolar reaction of N-ylides: access to benzo-fused indolizines DOI

Limin Zhao,

Wen Li, Jiali Liu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(48), P. 9604 - 9608

Published: Jan. 1, 2022

An efficient metal-free annulative vinylene transfer protocol for the synthesis of benzo-fused indolizines via 1,3-dipolar cycloadditions N-ylides with carbonate has been developed. Vinylene serves as an acetylene surrogate without any external oxidant involved. This transformation leads to direct construction versatile indolizine derivatives in moderate good yields.

Language: Английский

Citations

19