Decatungstate-photocatalyzed direct acylation of N-heterocycles with aldehydes

Zhang, Zhiyang; Cheng, Fukun; Ma, Xinyu; Sun, Kai; Huang, Xianqiang; An, Jiangzhen; Peng, Mei; Chen, Xiaolan; Yu, Bing

doi:10.1039/d4gc00534a

Green Chem.

2024

DOI: 10.1039/d4gc00534a

|View full text |Cite

Decatungstate-photocatalyzed direct acylation of N-heterocycles with aldehydes

Zhiyang Zhang,

Fukun Cheng,

Xinyu Ma

et al.

Abstract: A novel photocatalytic acylation strategy was developed harnessing tetrabutylammonium decatungstate (TBADT) as a hydrogen atom transfer (HAT) photocatalyst to facilitate the direct coupling of aldehydes with N-heterocycles at ambient temperature.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2024

2025

Publication Types

Select...

Article5

Relationship

Self Cite0

Independent5

Authors

Journals

Cited by 15 publications

References 70 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Visible‐Light‐Induced C−H Silylation of Azauracils with Hydrosilanes

Yu,

You,

et al. 2024

Adv Synth Catal

View full text Add to dashboard Cite

A C–H silylation of azauracils was developed via the combination of organic photoredox and hydrogen atom transfer (HAT) catalysis. Using 1,2,3,5‐tetrakis(carbazol‐9‐yl)‐4,6‐dicyanobenzene (4CzIPN) as the photocatalyst, quinuclidine as the HAT catalyst, and silanes as the silyl radical sources, a variety of silylated azauracils were synthesized in 43‐87% yields. Moreover, pyrazinone, cinnolinone, and chromone were also compatible with this catalytic system. The reaction is suitable for late‐stage functionalization of drugs and complex molecules, and the transformation can be easily scaled up to the gram level. Mechanistic studies suggest that the silylation reaction is likely to proceed through a radical mechanism.

show abstract

Visible‐Light‐Induced C−H Silylation of Azauracils with Hydrosilanes

Yu,

You,

et al. 2024

Adv Synth Catal

View full text Add to dashboard Cite

show abstract

Cu(I)‐Catalyzed Silylation and Germylation of Azauracils

Mahato,

Ghosh,

Hajra

2024

Chemistry A European J

View full text Add to dashboard Cite

The current study demonstrates a Cu(I) catalyzed direct C(sp2)‐H silylation and germylation of azauracil using triphenylsilane and triphenylgermane. A broad scope, excellent functional group tolerance, and suitability for large‐scale reactions are exhibited in this protocol. Moreover, this method can be readily applied to structurally complex bioactive molecules. Experimental results suggest a radical mechanistic pathway for the reaction.

show abstract

Photochemical‐, Electrochemical‐, and Photoelectrochemical‐ Catalyzed Hydrogen Atom Transfer from Aldehydes to Acyl Radicals and Their Transformations

Wang,

Wang

et al. 2024

Eur J Org Chem

View full text Add to dashboard Cite

Acyl radical has assumed an eminent position in the synthetic chemistry due to its unique and often highly reactive nature. Using aldehyde as acyl radical source does not require the prefunctionalization of substrate. Furthermore, the formation of acyl radical can be achieved through a hydrogen atom transfer (HAT) process. In recent years, photochemical‐, electrochemical‐, and photoelectrochemical‐catalyzed intermolecular HAT from aldehydes have been regarded as mild and sustainable routes for the generation of acyl radicals. Herein, we discuss some of the key advancements in the past 6 years in photo‐, electro‐, and photoelectro‐catalyzed generation of acyl radicals from aldehydes and their utilization. We also highlight the mechanistic insights that have emerged from these transformations.

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.

Decatungstate-photocatalyzed direct acylation of N-heterocycles with aldehydes

Abstract: A novel photocatalytic acylation strategy was developed harnessing tetrabutylammonium decatungstate (TBADT) as a hydrogen atom transfer (HAT) photocatalyst to facilitate the direct coupling of aldehydes with N-heterocycles at ambient temperature.

Cited by 15 publications

References 70 publications

Visible‐Light‐Induced C−H Silylation of Azauracils with Hydrosilanes

Visible‐Light‐Induced C−H Silylation of Azauracils with Hydrosilanes

Cu(I)‐Catalyzed Silylation and Germylation of Azauracils

Photochemical‐, Electrochemical‐, and Photoelectrochemical‐ Catalyzed Hydrogen Atom Transfer from Aldehydes to Acyl Radicals and Their Transformations

Contact Info

Product

Resources

About