Comparative study of 1:1 Lewis acid–base adducts between Cp2M(L)H (M = V, Nb, Ta; L = CO, C2H4, P(CH3)3) and BF3/AlF3

Wang, Jia; Sun, ZhengMing; Li, Xiaoyan

doi:10.1007/s00214-019-2493-3

Cited by 8 publications

(10 citation statements)

References 47 publications

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“…The reaction time is shorter in the case of polymeric catalyst (3‐4 h) than in the case of HPIL (5 h). The presence of hydroxyl groups in the catalyst structure allows the hydrogen bonding between hydroxyl groups and PO . The experimental and theoretical studies of mechanistic details of the cycloaddition revealed that the barrier height of ring‐opening step by using hydroxyl‐functionalized ILs as catalysts is much lower than in the case of using the corresponding traditional ILs.…”

Section: The Use Of Phosphonium Ionic Liquids As Catalystsmentioning

confidence: 99%

Phosphonium‐Based Ionic Liquids Used as Reagents or Catalysts

2019

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The role and enlarged importance of ionic liquids (ILs) in chemical reactions were already exhaustively demonstrated. The aim of this review is to promote the family of the phosphonium‐based ILs used as reagents and catalysts, which gained increased interest in the last decade. The common and beneficial properties of ILs refer to their negligible vapour pressure, non‐toxicity, reusability, and high thermal stability. Therefore, phosphonium‐based ionic liquids are used successfully as catalysts and reagents in many chemical reactions, and additionally allow the syntheses in mild reaction conditions. Phosphonium ILs have proved their catalytic efficiency in many reactions such as epoxidation of olefins and allylic alcohol, in synthesis of alpha‐aminophosphonates, beta‐ketophosphonates, nitrogen‐containing bisphosphonates, the Michaelis‐Arbuzov reactions, esterification, coupling reaction, aromatic chlorination, dehydrogenation. The major advantage of phosphonium‐based ILs used as catalysts is that they can be reused with only little loss of catalytic activity. Phosphonium ILs revealed their potential as Wittig reagents, halogenation reagents for bromination and bromo‐chlorination reactions with alkenes and alkynes, as monomer and as initiator in frontal polymerization of acrylates. From the literature data, it can be concluded that due to their structure and physical‐chemical properties phosphonium ILs can be tailored function of their purpose.

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Section: The Use Of Phosphonium Ionic Liquids As Catalystsmentioning

confidence: 99%

Phosphonium‐Based Ionic Liquids Used as Reagents or Catalysts

2019

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“…Based on the above experimental data and previous reports, [19,20,33,34] a plausible reaction mechanism for visible‐light‐mediated sulfonylation/cyclization reaction was described in Scheme 4. Under the irradiation of 5 W blue LEDs, the photosensizer fac ‐[Ir III (ppy) 3 ] was excited to fac ‐[Ir III (ppy) 3 ]*, which was readily oxidated by p ‐toluene sulfonyl chloride 2 a to produce the corresponding radical species A .…”

Section: Methodsmentioning

confidence: 69%

“…In 2019, Yu and co‐workers realized the rapid preparation of perfluoroalkyl‐substituted benzimidazo[2,1‐ a ]isoquinolin‐6(5 H )‐ones via a metal‐free visible‐light‐promoted radical cyclization process (Scheme 1,a) [19] . After then, a novel visible‐light‐induced diarylation of N ‐methacryloyl‐2‐arylbenzoimidazoles in the presence of aryl diazonium salts was reported by Li's group (Scheme 1,b) [20] . Another elegant visible‐light‐mediated transformation for the synthesis of various benzo[4,5]imidazo[2,1‐ a ]isoquinolin‐6(5 H )‐one derivatives with CH 2 CN/CF 2 COOEt/CF 3 was disclosed by Guan et al (Scheme 1,c) [21] .…”

Section: Methodsmentioning

confidence: 99%

Visible‐Light‐Driven Sulfonylation/Cyclization to Access Sulfonylated Benzo[4,5]imidazo[2,1‐a]isoquinolin‐6(5H)‐ones

Wang

Sun

Huang

et al. 2021

Chemistry An Asian Journal

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Visible‐light‐driven sulfonylation/cyclization of N‐methacryloyl‐2‐phenylbenzoimidazoles has been successfully developed. Using commercially available sulfonyl chloride as sulfonylation reagent, a wide range of sulfonylated benzo[4,5]imidazo[2,1‐a]isoquinolin‐6(5H)‐ones with potential antitumor activity were provided in acceptable to excellent yields. This method has the advantages of mild reaction conditions and outstanding functional group tolerance, and provides a new strategy for the development of potential antitumor lead compounds.

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“…Using aryl diazonium salts as aryl radical precursors, Wang and co‐workers achieved the construction of arylated benzimidazo[2,1‐ a ]isoquinolin‐6(5 H )‐ones under photocatalytic conditions (Scheme 80). [142] …”

Section: Cyclization Of Alkene‐tethered 2‐arylindoles and 2‐aryl Benz...mentioning

confidence: 99%

“…Using aryl diazonium salts as aryl radical precursors, Wang and co-workers achieved the construction of arylated benzimidazo[2,1-a]isoquinolin-6(5H)-ones under photocatalytic conditions (Scheme 80). [142] In 2019, Xu and co-workers reported a visible-light-induced radical cascade cyclization of N-acryloyl-2-phenylindoles with acyl chlorides for the delivering of acylated indolo[2,1a]isoquinolines (Scheme 81a). [143] Later, aryl aldehydes, [144] αketo acids [145] and oxamic acids [146] were also successfully utilized in the cascade cyclization of 2-aryl-N-acryloyl indoles under metal-free or visible-light-promoted conditions (Scheme 81b, c).…”

Section: Cyclization Of Alkene-tethered 2-arylindoles and 2-aryl Benz...mentioning

confidence: 99%

Radical Cascade Cyclization of Alkene‐Tethered Compounds: Versatile Approach towards Ring‐Fused Polycyclic Structures

Liu

Wang

2023

Asian J Org Chem

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Ring-fused polycyclic structures widely exist in a myriad of natural products and pharmaceutical molecules. Consequently, the construction of such structures from readily available substrates becomes an important researching topic in organic synthesis. Triggered by the addition of radicals to the (activated or unactivated) double bonds in alkenes, the subsequent intramolecular addition/cyclization leads to polycyclic compounds. Following this procedure, a variety of functionalized ring-fused structures were formed. Great achievements have been witnessed recently. Those works provided efficient, atom economy, and operational simple approaches toward versatile functionalized polycyclic structures from readily available alkene-based substrates.Here, we summarized the recent achievements on the formation of ring-fused polycyclic structures via the radicaltriggered cascade reactions of alkenes. Construction of polycyclic structures with no less than 3 fused rings developed during the last decade were included in this Review, corresponding mechanisms were also discussed.

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Comparative study of 1:1 Lewis acid–base adducts between Cp2M(L)H (M = V, Nb, Ta; L = CO, C2H4, P(CH3)3) and BF3/AlF3

Cited by 8 publications

References 47 publications

Phosphonium‐Based Ionic Liquids Used as Reagents or Catalysts

Phosphonium‐Based Ionic Liquids Used as Reagents or Catalysts

Visible‐Light‐Driven Sulfonylation/Cyclization to Access Sulfonylated Benzo[4,5]imidazo[2,1‐a]isoquinolin‐6(5H)‐ones

Radical Cascade Cyclization of Alkene‐Tethered Compounds: Versatile Approach towards Ring‐Fused Polycyclic Structures

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