Formation of synthetically relevant CF<sub>3</sub>-substituted phenonium ions in superacid media

Fernandes, Anthony J.; Michelet, Bastien; Panossian, Armen; Martin‐Mingot, Agnès; Leroux, Frédéric R.; Thibaudeau, Sébastien

doi:10.1039/d1ra04901a

RSC Adv.

2021

DOI: 10.1039/d1ra04901a

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Formation of synthetically relevant CF₃-substituted phenonium ions in superacid media

Anthony J. Fernandes

Bastien Michelet

Armen Panossian

et al.

Abstract: Under superacidic conditions, CF3-substituted phenonium ions can be generated to furnish original CF3-substituted dihydrostilbenes of interest.

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Cited by 3 publications

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Cationic [1,5]‐Aryl Migrations of Propargyl Benzyl Ethers – A Stereospecific Approach to E‐ and Z‐Tetrasubstituted Olefins

Sadhukhan,

Nair,

Baire

2024

Adv Synth Catal

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Abstract. Herein we report the discovery and development of the first example of a cationic [1,5]‐aryl migration reaction, through an unprecedented phenonium ions. This reaction does not require any acid, base, transition metal‐based catalyst or promoter, instead promoted by the water activated NXS reagents. It provides a highly diastereoselective and rapid access to the medicinally and biologically important tetra‐substituted olefins (allyl alcohols). The involvement of an ipso‐carbon, as well as the phenonium ion during this novel, cationic [1,5]‐aryl migration was strongly supported by the isolation of 2‐oxaspiro[5.5]undecane‐9‐ones. This methodology is highly tolerable for a wide range of propargyl‐benzyl ethers, resulting in a selective construction of structurally divergent library of mono‐halo‐tricarbon‐substituted alkenes. Synthetic application has also been demonstrated by converting two isomeric‐iodo‐olefins to respective E‐ and Z‐isomers of tamoxifen in a stereospecific manner.

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Cationic [1,5]‐Aryl Migrations of Propargyl Benzyl Ethers – A Stereospecific Approach to E‐ and Z‐Tetrasubstituted Olefins

Sadhukhan,

Nair,

Baire

2024

Adv Synth Catal

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Cobalt‐Catalyzed Wagner–Meerwein Rearrangements with Concomitant Nucleophilic Hydrofluorination

Hoogesteger,

Murdoch,

Cordes

et al. 2023

Angewandte Chemie

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We report a cobalt‐catalyzed Wagner–Meerwein rearrangement of gem‐disubstituted allylarenes that generates fluoroalkane products with isolated yields up to 84 %. Modification of the counteranion of the N‐fluoropyridinium oxidant suggests the substrates undergo nucleophilic fluorination during the reaction. Subjecting the substrates to other known metal‐mediated hydrofluorination procedures did not lead to observable 1,2‐aryl migration. Thus, indicating the unique ability of these cobalt‐catalyzed conditions to generate a sufficiently reactive electrophilic intermediate capable of promoting this Wagner–Meerwein rearrangement.

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Cobalt‐Catalyzed Wagner–Meerwein Rearrangements with Concomitant Nucleophilic Hydrofluorination

Hoogesteger,

Murdoch,

Cordes

et al. 2023

Angew Chem Int Ed

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Formation of synthetically relevant CF₃-substituted phenonium ions in superacid media

Abstract: Under superacidic conditions, CF3-substituted phenonium ions can be generated to furnish original CF3-substituted dihydrostilbenes of interest.

Cited by 3 publications

References 66 publications

Cationic [1,5]‐Aryl Migrations of Propargyl Benzyl Ethers – A Stereospecific Approach to E‐ and Z‐Tetrasubstituted Olefins

Cationic [1,5]‐Aryl Migrations of Propargyl Benzyl Ethers – A Stereospecific Approach to E‐ and Z‐Tetrasubstituted Olefins

Cobalt‐Catalyzed Wagner–Meerwein Rearrangements with Concomitant Nucleophilic Hydrofluorination

Cobalt‐Catalyzed Wagner–Meerwein Rearrangements with Concomitant Nucleophilic Hydrofluorination

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Formation of synthetically relevant CF3-substituted phenonium ions in superacid media

Abstract: Under superacidic conditions, CF3-substituted phenonium ions can be generated to furnish original CF3-substituted dihydrostilbenes of interest.

Cited by 3 publications

References 66 publications

Cationic [1,5]‐Aryl Migrations of Propargyl Benzyl Ethers – A Stereospecific Approach to E‐ and Z‐Tetrasubstituted Olefins

Cationic [1,5]‐Aryl Migrations of Propargyl Benzyl Ethers – A Stereospecific Approach to E‐ and Z‐Tetrasubstituted Olefins

Cobalt‐Catalyzed Wagner–Meerwein Rearrangements with Concomitant Nucleophilic Hydrofluorination

Cobalt‐Catalyzed Wagner–Meerwein Rearrangements with Concomitant Nucleophilic Hydrofluorination

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Product

Resources

About

Formation of synthetically relevant CF₃-substituted phenonium ions in superacid media