Palladium-catalyzed carbonylative synthesis of carboxamide substituted 2-pynones from methyl enynoates and nitroarenes

Wen, Dan; Ge, Xing; Miao, Ren-Guan; Qi, Xinxin; Wu, Xiao‐Feng

doi:10.1016/j.jcat.2023.08.011

Journal of Catalysis

2023

DOI: 10.1016/j.jcat.2023.08.011

|View full text |Cite

Palladium-catalyzed carbonylative synthesis of carboxamide substituted 2-pynones from methyl enynoates and nitroarenes

Dan Wen

Xing Ge

Ren-Guan Miao

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...

Article2

Relationship

Self Cite0

Independent2

Authors

Journals

Cited by 2 publications

References 39 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Palladium‐Catalyzed Cyclization/Thiocarbonylation for the Synthesis of Thioester‐Substituted Benzofurans with S‐Aryl Thioformates as the Thioester Sources

Ge,

Lin,

et al. 2024

Eur J Org Chem

View full text Add to dashboard Cite

A palladium‐catalyzed cyclization and thiocarbonylation reaction has been disclosed for the synthesis of thioesters‐containing benzofurans. By using S‐aryl thioformates as efficient and convenient thioester surrogates, a variety of thioesters‐functionalized benzofurans are formed in moderate to excellent yields with very good functional group tolerance. This protocol features mild reaction conditions, broad substrate scope, and no manipulation of toxic CO gas and odorous thiols.

show abstract

Palladium‐Catalyzed Cyclization/Thiocarbonylation for the Synthesis of Thioester‐Substituted Benzofurans with S‐Aryl Thioformates as the Thioester Sources

Ge,

Lin,

et al. 2024

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

Palladium-Catalyzed Difluorocarbene Transfer Enabled Divergent Synthesis of γ-Butenolides and Ynones from Iodobenzene and Terminal Alkynes

Sheng,

Chen,

Song

2024

J. Am. Chem. Soc.

View full text Add to dashboard Cite

Herein, we report a ligand-controlled palladiumcatalyzed method that enables the synthesis of ynones and γbutenolides with excellent regioselectivity from the same set of readily available aryl iodides, aryl acetylenes, and BrCF 2 CO 2 K. In this reaction, the [Pd II ]�CF 2 does demonstrate electrophilicity and can generate CO readily when reacting with H 2 O. It is environmentally friendly and safe compared to traditional methods, and the current protocol enables us to afford ynones and γbutenolides in high yields with excellent functionality tolerance. Moreover, esters can also be obtained with corresponding phenols and alcohols utilizing this strategy. The success of late-stage functionalization of bioactive compounds further illustrates the synthetic utility of this protocol in material development and drug discovery.

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.

Palladium-catalyzed carbonylative synthesis of carboxamide substituted 2-pynones from methyl enynoates and nitroarenes

Cited by 2 publications

References 39 publications

Palladium‐Catalyzed Cyclization/Thiocarbonylation for the Synthesis of Thioester‐Substituted Benzofurans with S‐Aryl Thioformates as the Thioester Sources

Palladium‐Catalyzed Cyclization/Thiocarbonylation for the Synthesis of Thioester‐Substituted Benzofurans with S‐Aryl Thioformates as the Thioester Sources

Palladium-Catalyzed Difluorocarbene Transfer Enabled Divergent Synthesis of γ-Butenolides and Ynones from Iodobenzene and Terminal Alkynes

Contact Info

Product

Resources

About