Access to Benzo[a]carbazoles and Indeno[1,2-c]quinolines by a Gold(I)-Catalyzed Tunable Domino Cyclization of Difunctional 1,2-Diphenylethynes

Peng, Xiaoshi; Zhu, Lifeng; Hou, Yuqian; Pang, Yadong; Li, Yangming; Fu, Jiayue; Yang, Lu; Lin, Bin; Liu, Yongxiang; Cheng, Maosheng

doi:10.1021/acs.orglett.7b01358

Cited by 31 publications

(15 citation statements)

References 41 publications

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“…Diisocyanides 1a and 1b (Schemes S1 and S2) were prepared according to the synthetic procedures in the literature. − Inspired by the preparation method of 2-iodoaniline, , bis(2-iodoaniline)s 2a – 2d (Schemes S3 and S4) were prepared for the first time as far as we know.…”

Section: Resultsmentioning

confidence: 99%

CO₂-Involved and Isocyanide-Based Three-Component Polymerization toward Functional Heterocyclic Polymers with Self-Assembly and Sensing Properties

et al. 2021

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CO 2 utilization has been a hot research topic in academic and industrial respects. Besides converting CO 2 into chemicals and fuels, incorporating it into the polymers to construct functional materials is another promising strategy. However, the CO 2 -involved polymerization techniques should be further developed. In this work, a facile and efficient CO 2 -involved multicomponent polymerization is successfully developed. The reaction of monomers of CO 2 , isocyanides and 2-iodoanilines readily produces soluble and thermally stable poly(benzoyleneurea)s with well-defined structures under mild conditions. Thanks to the formed amide groups in the heterocyclic units in the main-chains, the resultant polymers could self-assemble into spheres with sizes between 200 and 1000 nm. The polymers containing tetraphenylethylene (TPE) unit show the unique aggregation-enhanced emission (AEE) features, which could be used to visualize the self-assembly process and morphologies under UV irradiation, and serve as fluorescence probe to selectively and sensitively detect Au 3+ ions. Notably, the polymers containing cis-and trans-TPE units exhibit different behaviors in self-assembly and limit of detection for Au 3+ ions due to the different intermolecular interactions. Thus, this work not only provides a new strategy for CO 2 utilization but also furnishes a series of functional heterocyclic polymers for diverse applications. File list (3) download file view on ChemRxiv Manuscript.docx (18.84 MiB) download file view on ChemRxiv Manuscript -Anjun Qin.pdf (1.92 MiB) download file view on ChemRxiv Supporting information.pdf (2.46 MiB) CO 2 -Involved and Isocyanide-based Threecomponent Polymerization toward Functional

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Section: Resultsmentioning

confidence: 99%

CO₂-Involved and Isocyanide-Based Three-Component Polymerization toward Functional Heterocyclic Polymers with Self-Assembly and Sensing Properties

et al. 2021

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“…Diisocyanides 1a and 1b (Scheme S1 and S2) were prepared according to the synthetic procedures given in literature. [38][39][40] Inspired by the preparation method of 2iodoaniline, 41,42 bis(2-iodoaniline)s 2a-2d (Scheme S3 and S4) were prepared for the first time as far as we know.…”

Section: Resultsmentioning

confidence: 99%

CO2-Involved and Isocyanide-based Three-component Polymerization toward Functional Heterocyclic Polymers with Self-assembly and Sensing Properties

Liu¹,

Song²,

Wang³

et al. 2021

Preprint

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CO2 utilization has been a hot research topic in academic and industrial respects. Besides converting CO2 into chemicals and fuels, incorporating it into the polymers to construct functional materials is another promising strategy. However, the CO2-involved polymerization techniques should be further developed. In this work, a facile and efficient CO2-involved multicomponent polymerization is successfully developed. The reaction of monomers of CO2, isocyanides and 2-iodoanilines readily produces soluble and thermally stable <a>poly(</a><a>benzoyleneurea</a>)s with well-defined structures under mild conditions. Thanks to the formed amide groups in the heterocyclic units in the main-chains, the resultant polymers <a>could self-assemble into </a>spheres with sizes between 200 and 1000 nm. <a>The polymers containing tetraphenylethylene (TPE) unit show the unique aggregation-enhanced emission (AEE) features, which could be used to visualize the self-assembly process and morphologies under UV irradiation</a><a>, and serve as fluorescence probe to selectively and sensitively detect Au3+ ions. </a>Notably, the polymers containing cis- and trans-TPE units exhibit different behaviors in self-assembly and limit of detection for <a>Au3+ ions</a> due to the different intermolecular interactions. Thus, this work not only provides a new strategy for CO2 utilization but also furnishes a series of functional heterocyclic polymers for diverse applications.

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“…When o ‐alkenyl moieties are present in the 2‐alkynylanilines 161 , a reactivity switch could be observed (Scheme 51). [150] Thus, it has been shown that depending on the substituent at a nitrogen atom, either five‐ or six‐membered heterocycle could be formed. In case of N ‐tosylated amine (R 3 =Ts), the formation of indole 162 takes place, followed by carbocyclization.…”

Section: Synthesis Of Polycyclic Systemsmentioning

confidence: 99%

2‐(Alkynyl)anilines and Derivatives — Versatile Reagents for Heterocyclic Synthesis

2022

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The transformations of 2‐alkynylanilines and their derivatives into heterocycles are surveyed. Depending on the substituents, catalysts, and reaction conditions, these substrates can be converted into indoles, quinolines, indolines, oxindoles, indoxiles, various polycyclic compounds, etc. This review aims to generalize and assess the patterns of reactivity, selectivity, and applicability of 2‐(alkynyl)anilines in heterocyclic chemistry. The review is divided into sections in accordance with the produced heterocycle. In summary, the title substrates are capable of cyclizing not only into five‐ and six‐membered rings, but also to produce seven‐ and even eight‐membered ring systems. The preparation of 2‐(alkynyl)anilines is not covered.

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Access to Benzo[a]carbazoles and Indeno[1,2-c]quinolines by a Gold(I)-Catalyzed Tunable Domino Cyclization of Difunctional 1,2-Diphenylethynes

Cited by 31 publications

References 41 publications

CO₂-Involved and Isocyanide-Based Three-Component Polymerization toward Functional Heterocyclic Polymers with Self-Assembly and Sensing Properties

CO₂-Involved and Isocyanide-Based Three-Component Polymerization toward Functional Heterocyclic Polymers with Self-Assembly and Sensing Properties

CO2-Involved and Isocyanide-based Three-component Polymerization toward Functional Heterocyclic Polymers with Self-assembly and Sensing Properties

2‐(Alkynyl)anilines and Derivatives — Versatile Reagents for Heterocyclic Synthesis

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Access to Benzo[a]carbazoles and Indeno[1,2-c]quinolines by a Gold(I)-Catalyzed Tunable Domino Cyclization of Difunctional 1,2-Diphenylethynes

Cited by 31 publications

References 41 publications

CO2-Involved and Isocyanide-Based Three-Component Polymerization toward Functional Heterocyclic Polymers with Self-Assembly and Sensing Properties

CO2-Involved and Isocyanide-Based Three-Component Polymerization toward Functional Heterocyclic Polymers with Self-Assembly and Sensing Properties

CO2-Involved and Isocyanide-based Three-component Polymerization toward Functional Heterocyclic Polymers with Self-assembly and Sensing Properties

2‐(Alkynyl)anilines and Derivatives — Versatile Reagents for Heterocyclic Synthesis

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Product

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CO₂-Involved and Isocyanide-Based Three-Component Polymerization toward Functional Heterocyclic Polymers with Self-Assembly and Sensing Properties

CO₂-Involved and Isocyanide-Based Three-Component Polymerization toward Functional Heterocyclic Polymers with Self-Assembly and Sensing Properties