Transition metal-free photocatalytic reductive deuteration of ketone derivatives

Cai, Jiaxin; Li, Yanjun; Ye, Ziqi; Wang, Wenqian; Lin, Yumei; Gong, Lei

doi:10.1016/j.gresc.2022.05.004

Green Synthesis and Catalysis

2023

DOI: 10.1016/j.gresc.2022.05.004

|View full text |Cite

Transition metal-free photocatalytic reductive deuteration of ketone derivatives

Jiaxin Cai

Yanjun Li

Ziqi Ye

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...

Article6

Relationship

Self Cite0

Independent6

Authors

Journals

Cited by 9 publications

(1 citation statement)

References 45 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…9 A powerful photocatalyst is required to be capable of participating in both SET reduction and SET oxidation events for the C–H functionalization process as well as sequential SET reductions for the dearomatization process. In addition, the reaction might encounter the chemoselective competition from reduction 10 or pinacol C–C coupling. 11 Furthermore, the diastereoselective issues should be addressed when multiple stereocenters are generated.…”

mentioning

confidence: 99%

Tunable C–H functionalization and dearomatization enabled by an organic photocatalyst

An,

Cui,

Zheng

et al. 2024

Chem. Sci.

View full text Add to dashboard Cite

show abstract

mentioning

confidence: 99%

Tunable C–H functionalization and dearomatization enabled by an organic photocatalyst

An,

Cui,

Zheng

et al. 2024

Chem. Sci.

View full text Add to dashboard Cite

show abstract

Recyclable Ag/g‐C₃N₄ Catalyzed Visible‐light Promoted Heterogeneous Synthesis of Unsymmetric Diaryl Chalcogenides

Ji,

Yi,

Zhou

et al. 2024

Asian J Org Chem

View full text Add to dashboard Cite

With Ag/g‐C3N4 semiconductor as the heterogeneous photocatalyst, the visible light promoted heterogeneous synthesis of unsymmetric diaryl chalcogenides could be achieved under additive‐free and mild conditions. A series of unsymmetric diaryl chalcogenides were generated in good to excellent yields with high functional group tolerance. The Ag/g‐C3N4 photocatalyst is easily recovered from the reaction mixture and reused at least 5 times, opening the way for larger‐scale industrial applications of this type of photocatalytic bond‐forming reactions.

show abstract

Robust Catalytic S_EAr H/D Exchange of Arenes with D₂O: Metal‐Free Deuteration of Natural Complexes and Drugs

Zhang,

Lv,

Ong

et al. 2024

Angewandte Chemie

View full text Add to dashboard Cite

A catalytic metal‐free approach for the H/D exchange in aromatic compounds using D2O as the terminal deuterating reagent has been developed. This metal‐free protocol employs a triaryl carbenium as the mediator and showcases a wide applicability in the late‐stage deuteration of various natural products and small‐molecule drugs. Gram‐scale deuteration was successfully demonstrated with β‐Estradiol, highlighting the method's practicability. Detailed mechanistic insights, supported by DFT calculations, unveiled the essential role of in‐situ generated acidic species in this electrophilic aromatic substitution process. This newly developed method offers a sustainable and versatile alternative to traditional metal‐catalyzed H/D exchange techniques, addressing challenges such as the use of expensive metals, impurity formation, and the necessity for residual metal removal from the final products.

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 photocatalytic reductive deuteration of ketone derivatives

Cited by 9 publications

References 45 publications

Tunable C–H functionalization and dearomatization enabled by an organic photocatalyst

Tunable C–H functionalization and dearomatization enabled by an organic photocatalyst

Recyclable Ag/g‐C₃N₄ Catalyzed Visible‐light Promoted Heterogeneous Synthesis of Unsymmetric Diaryl Chalcogenides

Robust Catalytic S_EAr H/D Exchange of Arenes with D₂O: Metal‐Free Deuteration of Natural Complexes and Drugs

Contact Info

Product

Resources

About

Transition metal-free photocatalytic reductive deuteration of ketone derivatives

Cited by 9 publications

References 45 publications

Tunable C–H functionalization and dearomatization enabled by an organic photocatalyst

Tunable C–H functionalization and dearomatization enabled by an organic photocatalyst

Recyclable Ag/g‐C3N4 Catalyzed Visible‐light Promoted Heterogeneous Synthesis of Unsymmetric Diaryl Chalcogenides

Robust Catalytic SEAr H/D Exchange of Arenes with D2O: Metal‐Free Deuteration of Natural Complexes and Drugs

Contact Info

Product

Resources

About

Recyclable Ag/g‐C₃N₄ Catalyzed Visible‐light Promoted Heterogeneous Synthesis of Unsymmetric Diaryl Chalcogenides

Robust Catalytic S_EAr H/D Exchange of Arenes with D₂O: Metal‐Free Deuteration of Natural Complexes and Drugs