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

|View full text |Cite

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.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2023

2024

Publication Types

Select...

Article3

Relationship

Self Cite0

Independent3

Authors

Journals

Cited by 3 publications

References 66 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

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

View full text Add to dashboard Cite

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.

show abstract

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

View full text Add to dashboard Cite

show abstract

Cobalt‐Catalyzed Wagner–Meerwein Rearrangements with Concomitant Nucleophilic Hydrofluorination

Hoogesteger,

Murdoch,

Cordes

et al. 2023

Angewandte Chemie

View full text Add to dashboard Cite

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.

show abstract

Cobalt‐Catalyzed Wagner–Meerwein Rearrangements with Concomitant Nucleophilic Hydrofluorination

Hoogesteger,

Murdoch,

Cordes

et al. 2023

Angew Chem Int Ed

View full text Add to dashboard Cite

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

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

Contact Info

Product

Resources

About

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

Contact Info

Product

Resources

About

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