SnCl<sub>4</sub> or TiCl<sub>4</sub>: highly efficient catalysts for the detetrahydropyranylation and demethoxymethylation of phenolic ethers and sequential one-pot asymmetric synthesis of 3-aryl-2-hydroxy-2,3-dihydroindan-1-ones from chalcone epoxides

Ahmed, Naseem; Pathe, Gulab Khushalrao; Jheeta, Sohan

doi:10.1039/c5ra10499h

Cited by 14 publications

(5 citation statements)

References 107 publications

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“…172 In 2015, Ahmed and co-workers reported the FC reaction of racemic and enantiomerically enriched chalcone epoxide substrates via an EAC strategy with catalytic TiCl 4 or SnCl 4 and resulting trans-3-aryl-2-hydroxy-2,3-dihydro-1H-inden-1-ones. 173 Furthermore, Das reviewed FC intramolecular C-C bondforming reactions of arene or heteroarene nucleophiles with tethered epoxides starting materials. 174 In 2010, Qu and Li studied the FC alkylation of arene nucleophiles with epoxides promoted by HFIP or water under refluxing conditions.…”

Section: Short Review Synthesismentioning

confidence: 99%

Recent Advancements in Typical Friedel–Crafts Alkylation Reactions Focused on Targeting Arene Nucleophiles

Hazra,

Singh

2023

Synthesis

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This review delves into recent advances and significant breakthroughs in the field of the catalytic Friedel–Crafts alkylation of targeted arenes or heteroarenes. Though a few earlier literatures are referenced, the main emphasis of this review focuses on the literature mainly published between 2015 and March 2023.1 Introduction2 History and Background3 Alcohols as Alkylating Agents4 Aldehydes and Ketones as Alkylating Agents5 Alkyl Fluorides as Alkylating Agents6 Epoxides as Alkylating Agents7 Cyclopropanes as Alkylating Agents8 Conclusion and Outlook

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Section: Short Review Synthesismentioning

confidence: 99%

Recent Advancements in Typical Friedel–Crafts Alkylation Reactions Focused on Targeting Arene Nucleophiles

Hazra,

Singh

2023

Synthesis

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“…According to the literature, ring opening of styrene oxide by arenes with moderate nucleophilicities occurs only in the presence of strong Lewis acids (AlCl 3 , SnCl 4 , and others) or strong Brønsted acids (e.g., trifluoromethanesulfonic acid). In 2010, we reported that HFIP promotes intramolecular Friedel–Crafts reactions between arenes and epoxides .…”

Section: Resultsmentioning

confidence: 99%

Studies on the Origin of the Stabilizing Effects of Fluorinated Alcohols and Weakly Coordinated Fluorine-Containing Anions on Cationic Reaction Intermediates

Tian

2022

J. Org. Chem.

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Many synthetic methods that use fluorinated alcohols as solvents have been reported, and the fluorinated alcohols have been found to be crucial to the success of these methods. In addition, there have been reports indicating that adding a weakly coordinated fluorine-containing anion, such as BF 4− , PF 6 − , or SbF 6 − , to fluorinated alcohols can improve yields. The boosting effect of fluorinated alcohols is attributed mainly to hydrogen bond activation. A few studies have suggested that the very polar fluorinated alcohols can stabilize cationic reaction intermediates. However, how they do so and why weakly coordinated fluorine-containing anions improve yields have not been studied in depth. Here, we used quaternary ammonium cations, a quaternary phosphonium cation, and a triaryl-substituted carbocation as models for short-lived cationic intermediates and studied the possible interactions of these cations with fluorinated alcohols and BF 4 − , PF 6 − , or SbF 6 − . On the basis of the results, we propose that the C−F dipoles of fluorinated alcohols and the E−F dipoles (where E is B, P, or Sb) of weakly coordinated fluorinecontaining anions stabilized these cations by intermolecular charge−dipole interactions. We deduced that in the same fashion the C−F and E−F dipoles can thermodynamically stabilize cationic reaction intermediates.

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“…Ahmed and co‐workers reported an efficient protocol for the detetrahydropyranylation and demethoxymethylation of phenolic ethers and the stereoselective synthesis of trans ‐2‐hydroxy‐3‐aryl‐1‐indanone derivatives 54 [46] . The reaction proceeds via sequential ring opening of the chalcone epoxides 53 and intramolecular Friedel‐Crafts alkylation in the presence of SnCl 4 (or TiCl 4 ) catalyst (Scheme 18).…”

Section: Acid‐catalyzed Synthesismentioning

confidence: 99%

Transition‐Metal‐Free Synthesis of 1‐Indanone Skeleton: A Brief Update

Das¹

2021

ChemistrySelect

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Transition‐metal‐free carbon‐carbon bond forming reactions have drawn great interest because they are operationally simple, cost‐effective and environmentally benign. However, the construction of indanone core under metal‐free condition has been long‐standing challenges to organic chemists. In this article, recent advances (2015–2021) in transition‐metal‐free strategies towards 1‐indanone skeletons are reviewed and they are classified as acid‐catalyzed, base‐catalyzed, organocatalytic and catalyst‐free methods. In most cases, mechanisms for the transformations and stereochemical aspects of the product formation have been demonstrated.

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SnCl₄ or TiCl₄: highly efficient catalysts for the detetrahydropyranylation and demethoxymethylation of phenolic ethers and sequential one-pot asymmetric synthesis of 3-aryl-2-hydroxy-2,3-dihydroindan-1-ones from chalcone epoxides

Abstract: SnCl4 or TiCl4 catalysts provide a rapid and efficient detetrahydropyranylation and demethoxymethylation of phenolic ethers and a sequential one-pot intramolecular Friedel–Crafts alkylation of chalcone epoxides under mild reaction conditions.

Cited by 14 publications

References 107 publications

Recent Advancements in Typical Friedel–Crafts Alkylation Reactions Focused on Targeting Arene Nucleophiles

Recent Advancements in Typical Friedel–Crafts Alkylation Reactions Focused on Targeting Arene Nucleophiles

Studies on the Origin of the Stabilizing Effects of Fluorinated Alcohols and Weakly Coordinated Fluorine-Containing Anions on Cationic Reaction Intermediates

Transition‐Metal‐Free Synthesis of 1‐Indanone Skeleton: A Brief Update

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SnCl4 or TiCl4: highly efficient catalysts for the detetrahydropyranylation and demethoxymethylation of phenolic ethers and sequential one-pot asymmetric synthesis of 3-aryl-2-hydroxy-2,3-dihydroindan-1-ones from chalcone epoxides

Abstract: SnCl4 or TiCl4 catalysts provide a rapid and efficient detetrahydropyranylation and demethoxymethylation of phenolic ethers and a sequential one-pot intramolecular Friedel–Crafts alkylation of chalcone epoxides under mild reaction conditions.

Cited by 14 publications

References 107 publications

Recent Advancements in Typical Friedel–Crafts Alkylation Reactions Focused on Targeting Arene Nucleophiles

Recent Advancements in Typical Friedel–Crafts Alkylation Reactions Focused on Targeting Arene Nucleophiles

Studies on the Origin of the Stabilizing Effects of Fluorinated Alcohols and Weakly Coordinated Fluorine-Containing Anions on Cationic Reaction Intermediates

Transition‐Metal‐Free Synthesis of 1‐Indanone Skeleton: A Brief Update

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SnCl₄ or TiCl₄: highly efficient catalysts for the detetrahydropyranylation and demethoxymethylation of phenolic ethers and sequential one-pot asymmetric synthesis of 3-aryl-2-hydroxy-2,3-dihydroindan-1-ones from chalcone epoxides