Transition-metal-free and additive-free intermolecular hydroarylation of alkenes with indoles in hexafluoroisopropanol

Zhou, Changsheng; Huang, Ming; Yao, Yufeng; Chen, Chunyu; Yi, Xin; Yang, Ke-fang; Lai, Guo-Qiao; Xuan, Wenjing; Zhang, Pinglu

doi:10.1039/d3ob01570j

Org. Biomol. Chem.

2023

DOI: 10.1039/d3ob01570j

|View full text |Cite

Transition-metal-free and additive-free intermolecular hydroarylation of alkenes with indoles in hexafluoroisopropanol

Changsheng Zhou,

Ming Huang,

Yufeng Yao

et al.

Abstract: The hydroarylation of alkenes is arguably the most straightforward and atom-economical strategy for the construction of multi-aryl substituted alkanes, but systematic study is quite limited to transition metal catalysis. Here...

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2024

Publication Types

Select...

Article5

Relationship

Self Cite0

Independent5

Authors

Journals

Cited by 5 publications

References 77 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Brønsted Acid‐Catalyzed Markovnikov Hydroarylation of Arylcyclobutene: A Route to gem‐Diaryl‐Substituted Cyclobutanes

Wang,

Sun,

Wang

et al. 2024

Adv Synth Catal

View full text Add to dashboard Cite

A regioselective Markovnikov hydroarylation of arylcyclobutene has been developed using Brønsted acid catalysis through a protonation/Friedel‐Crafts sequence. The metal‐free catalytic reaction is operationally simple and feasible compared to previous reports that utilized elaborate arylcyclobutene and specific polyfluorinated reagents, affording a variety of gem‐diaryl‐ substituted arylcyclobutene in good to excellent yields. The possible mechanism of the reaction has been explored through step‐by‐step control experiments. This protocol involving indole in gem‐diaryl‐substituted cyclobutene scaffolds not only enriches the applications of Brønsted acid catalyzed hydroarylation, but also paves the way for a more extensive access to potential bioactive cyclobutanes structures.

show abstract

Brønsted Acid‐Catalyzed Markovnikov Hydroarylation of Arylcyclobutene: A Route to gem‐Diaryl‐Substituted Cyclobutanes

Wang,

Sun,

Wang

et al. 2024

Adv Synth Catal

View full text Add to dashboard Cite

show abstract

Cyclic Sulfoximines as Methyl and Perdeuteromethyl Transfer Agents and Their Applications in Photoredox Catalysis

Wu,

Goujon,

Pan

et al. 2024

Angewandte Chemie

View full text Add to dashboard Cite

Benzo[1,3,2]dithiazole‐1,1,3‐trioxides are bench‐stable and easy‐to‐use reagents. In photoredox catalysis, they generate methyl and perdeuteromethyl radicals which can add to a variety of radical acceptors, including olefins, acrylamides, quinoxalinones, isocyanides, enol silanes, and N‐Ts acrylamide. As byproduct, a salt is formed which can be regenerated to the original methylating agent. Flow chemistry provides an option for reaction scale‐up further underscoring the synthetic usefulness of these methylation reagents. Mechanistic investigations suggest a single‐electron transfer (SET) pathway induced by photoredox catalysis.

show abstract

Cyclic Sulfoximines as Methyl and Perdeuteromethyl Transfer Agents and Their Applications in Photoredox Catalysis

Wu,

Goujon,

Pan

et al. 2024

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.

Transition-metal-free and additive-free intermolecular hydroarylation of alkenes with indoles in hexafluoroisopropanol

Abstract: The hydroarylation of alkenes is arguably the most straightforward and atom-economical strategy for the construction of multi-aryl substituted alkanes, but systematic study is quite limited to transition metal catalysis. Here...

Cited by 5 publications

References 77 publications

Brønsted Acid‐Catalyzed Markovnikov Hydroarylation of Arylcyclobutene: A Route to gem‐Diaryl‐Substituted Cyclobutanes

Brønsted Acid‐Catalyzed Markovnikov Hydroarylation of Arylcyclobutene: A Route to gem‐Diaryl‐Substituted Cyclobutanes

Cyclic Sulfoximines as Methyl and Perdeuteromethyl Transfer Agents and Their Applications in Photoredox Catalysis

Cyclic Sulfoximines as Methyl and Perdeuteromethyl Transfer Agents and Their Applications in Photoredox Catalysis

Contact Info

Product

Resources

About