Photoinduced radical cascade brominative addition/spirocyclization of N-arylpropiolamides and CBr4 with O2 as oxidant

Wu, Zheng-Wei; Kong, Han-Han; Wei, Yong; Zhou, Wen-Chao; Wang, Long; Lu, Liang-Qiu; Yang, Qing-Qing

doi:10.1016/j.gresc.2024.01.004

Green Synthesis and Catalysis

2024

DOI: 10.1016/j.gresc.2024.01.004

|View full text |Cite

Photoinduced radical cascade brominative addition/spirocyclization of N-arylpropiolamides and CBr4 with O2 as oxidant

Zheng-Wei Wu,

Han-Han Kong,

Yong Wei

et al.

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...

Article3

Relationship

Self Cite0

Independent3

Authors

Journals

Cited by 3 publications

References 78 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Photocatalytic One-Pot Three-Component Reaction for the Regioselective Synthesis of Bromo-Substituted Pyrazoles

Zhang,

Li,

Wang

et al. 2024

J. Org. Chem.

View full text Add to dashboard Cite

A photocatalytic three-component cascade reaction of readily available enaminones, hydrazines, and CBr 4 for the synthesis of bromo-substituted pyrazoles in one pot has been demonstrated. This strategy involves intermolecular C-N/C-Br bond formation and represents an efficient approach to the construction of 4-bromo-substituted pyrazoles with high regioselectivity, broad substrate scope, good functional group tolerance, convenient operation, and mild reaction conditions. Mechanistic investigations show that this reaction proceeds via intermolecular cyclization of enaminones with hydrazines, followed by a regioselective bromination of pyrazoles using CBr 4 as a "Br" source.

show abstract

Photocatalytic One-Pot Three-Component Reaction for the Regioselective Synthesis of Bromo-Substituted Pyrazoles

Zhang,

Li,

Wang

et al. 2024

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

Halogen Radical-Enabled Dearomatization of N-Arylpropiolamides via Photoinduced Sequential Halogenation/Spirocyclization/Oxidation Process

Luo,

Jiang,

Luo

et al. 2024

J. Org. Chem.

View full text Add to dashboard Cite

Here we report a strategy that eliminates the need for photocatalysts and external additives, which provides an operable and mild method for halogen radical-enabled dearomatization of N-arylpropiolamides under an oxygen atmosphere at room temperature. The method is applicable to a wide range of substrates, extending beyond the limited scope of p-methoxyl Nphenylpropynamides. Furthermore, several functional synthetic intermediates and anticancer bioactive molecules were successfully derived from 3-halogenated azaspiro[4.5]trienones.

show abstract

Metal-Free Synthesis of 2-Benzylideneindolin-3-ones via a Nucleophilic/Rearrangement/Azide–Alkene Cascade Reaction

Tang,

Huang,

Wang

et al. 2024

Synlett

View full text Add to dashboard Cite

A metal-free synthesis of 2-benzylideneindolin-3-ones through a formal [4+1] annulation from o-azidobenzaldehydes and terminal alkynes has been developed. The method features operational simplicity, mild reaction conditions, and ready availability of starting materials. A broad range of 2-benzylideneindolin-3-ones were prepared in moderate to excellent yields. Mechanistic studies indicated that the reaction might proceed through a nucleophilic addition/rearrangement/azide–alkene cycloaddition pathway to produce 2-benzylideneindolin-3-ones.

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.

Photoinduced radical cascade brominative addition/spirocyclization of N-arylpropiolamides and CBr4 with O2 as oxidant

Cited by 3 publications

References 78 publications

Photocatalytic One-Pot Three-Component Reaction for the Regioselective Synthesis of Bromo-Substituted Pyrazoles

Photocatalytic One-Pot Three-Component Reaction for the Regioselective Synthesis of Bromo-Substituted Pyrazoles

Halogen Radical-Enabled Dearomatization of N-Arylpropiolamides via Photoinduced Sequential Halogenation/Spirocyclization/Oxidation Process

Metal-Free Synthesis of 2-Benzylideneindolin-3-ones via a Nucleophilic/Rearrangement/Azide–Alkene Cascade Reaction

Contact Info

Product

Resources

About