An Efficient and Green Synthesis of 1‐Indanone and 1‐Tetralone via Intramolecular Friedel–Crafts Acylation Reaction

Tran, Phuong Hoang; Huynh, Vy Hieu; Hansen, Poul Erik; Chau, Duy‐Khiem Nguyen; Lê, Thạch Ngọc

doi:10.1002/ajoc.201402274

Cited by 24 publications

(8 citation statements)

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“…[11] Particularly attractive" greener"m ethods combined the use of metal triflatec atalysts with non-conventionalt echniques, such as microwave (MW) irradiation or high intensity ultrasound (US) activation [12] and monomodalM W irradiation in ionic liquids (ILs) as the solvents. [13] Thisl atter approacha lso permitted the recycling of the catalysts withouta ppreciable loss of activity.…”

Section: Intramolecular Friedel-crafts-typec Yclization Reactionsmentioning

confidence: 99%

Recent Advances in the Synthesis of Indanes and Indenes

Gabriele

Mancuso

Veltri

2016

Chemistry A European J

176

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Indanes and indenes are among the most important carbocycles. Many indane and indene derivatives have shown important pharmacological activities, and the indane and indene nuclei are structural motifs present in several natural products of biological relevance. In spite of their importance, only a few reviews on their preparation methods have appeared so far in the literature, the most recent ones being published about ten years ago. The present Review is aimed at filling this gap, presenting some of the most important and innovative approaches to indanes and indenes that have been published in the course of the last ten years (coverage: from 2005 to May, 2015).

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Section: Intramolecular Friedel-crafts-typec Yclization Reactionsmentioning

confidence: 99%

Recent Advances in the Synthesis of Indanes and Indenes

Gabriele

Mancuso

Veltri

2016

Chemistry A European J

176

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“…Considering the pharmaceutical importance of tetralone derivatives, such as donepezil hydrochloride, a "green" intramolecular Friedel-Craft acylation was carried out with Tb(OTf) 3 catalyst, in ILs (bmim or bupy triflates), under MW irradiation, directly from carboxylic acid [90] (Scheme 27). Tb(OTf) 3 emerged as the catalyst of choice after a screening of 19metal triflates; moreover, it could be recovered and re-used three times, with only slight decrease in product isolated yield.…”

Section: Friedel-crafts Aromatic Substitutionsmentioning

confidence: 99%

The Beneficial Sinergy of MW Irradiation and Ionic Liquids in Catalysis of Organic Reactions

et al. 2017

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Abstract:The quest for sustainable processes is becoming more and more important, with catalysis playing a major role in improving atom economy and reducing waste. Organic syntheses with less need of protecting/de-protecting steps are highly desirable. The combination of microwave irradiation, as energy source, with ionic liquids, as both solvents and catalysts, offered interesting solutions in recent years. The literature data of the last 15 years concerning selected reactions are presented, highlighting the importance of microwave (MW) technology coupled with ionic liquids.

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“…Last, we recognized the reported syntheses of the precursor 1-indanone from bioderived cinnamic acid with heterogeneous catalysts, which serves as an important characteristic of any renewable polymer in order to reduce both CO 2 emissions and dependency on finite petroleum resources (Scheme S1). − …”

Section: Introductionmentioning

confidence: 99%

Lewis Pair Polymerization of Renewable Indenone to Erythro-Ditactic High-T_g Polymers with an Upcycling Avenue

et al. 2020

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Preparation and storage of biorenewable, monomeric indenone, much less the polymerization to a well-defined, high-molecular-weight polymer, is challenging because of antiaromaticity-driven radical autopolymerization. Herein, we report the successful preparation and subsequent Lewis pair polymerization (LPP) of indenone without autopolymerization side reactions using Lewis pairs consisting of sterically encumbered Lewis acid (LA) catalysts, such as B(C 6 F 5 ) 3 and bis(2,6-tert-butyl-4-methylphenoxy)methylaluminum and Lewis base initiators such as silyl ketene acetal and N-heterocyclic olefin nucleophiles. Thus, for the first time, the LPP enabled the synthesis of polyindenone (Pin) with high number-average molecular weight (M n = 1.72 × 10 5 g mol −1 ) and low dispersity (D̵ = 1.13). Observed correlations between the steric bulk of the LA catalyst and diastereoselectivity (57−75%) created the opportunity to model and investigate the relationships between β-substituted monomer motifs, catalyst steric accessibility, and the propagation stereodefining step for ensuing ditactic assignments. Through the increased erythro-diastereoselectivity, semicrystalline materials were produced with remarkably high glass-transition temperatures (T g = 307 °C), high thermal stability (T d,5% = 356 °C), and competitive transmittance (T %) and haziness values (T % = 85−88%, haze = 11%). Controlled pyrolysis of Pin upconverted it into versatile graphite oxide with 54% conversion, offering an upcycling avenue for Pin at the end of its life.

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An Efficient and Green Synthesis of 1‐Indanone and 1‐Tetralone via Intramolecular Friedel–Crafts Acylation Reaction

Cited by 24 publications

References 50 publications

Recent Advances in the Synthesis of Indanes and Indenes

Recent Advances in the Synthesis of Indanes and Indenes

The Beneficial Sinergy of MW Irradiation and Ionic Liquids in Catalysis of Organic Reactions

Lewis Pair Polymerization of Renewable Indenone to Erythro-Ditactic High-T_g Polymers with an Upcycling Avenue

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An Efficient and Green Synthesis of 1‐Indanone and 1‐Tetralone via Intramolecular Friedel–Crafts Acylation Reaction

Cited by 24 publications

References 50 publications

Recent Advances in the Synthesis of Indanes and Indenes

Recent Advances in the Synthesis of Indanes and Indenes

The Beneficial Sinergy of MW Irradiation and Ionic Liquids in Catalysis of Organic Reactions

Lewis Pair Polymerization of Renewable Indenone to Erythro-Ditactic High-Tg Polymers with an Upcycling Avenue

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Product

Resources

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Lewis Pair Polymerization of Renewable Indenone to Erythro-Ditactic High-T_g Polymers with an Upcycling Avenue