Cited by Photoredox-Catalyzed C–H Methylation of N-Heteroarenes Enabled by N,N-Dimethylethanolamine

Electrochemical C3-methylthiolation of imidazopyridines with dimethyl sulfoxide DOI

Zhaoyue Feng,

Y. C. Fan,

Congcong Qiang

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(6), P. 3517 - 3521

Published: Jan. 1, 2024

An electrochemical C-3 methylthiolation reaction of imidazo[1,2- a ]pyridines was achieved. The method used DMSO as both the methylthiolating reagent and solvent KI hydrogen atom transfer supporting electrolyte.

Language: Английский

Citations

Synergistic LMCT and Ni Catalysis for Methylative Cross-Coupling Using tert-Butanol: Modulating Radical Pathways via Selective Bond Homolysis DOI

Lingfei Duan, Yunzhi Lin, Qing An

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: April 18, 2025

Ligand-to-metal charge transfer (LMCT) excitation has emerged as a potent strategy for the selective generation of heteroatom-centered radicals, yet its full potential in modulating open-shell radical pathways remains underexplored. Here, we present photocatalytic methylative cross-coupling reaction that capitalizes on synergistic interplay between LMCT and Ni catalysis, enabling use tert-butanol an efficient benign methylating reagent. The electron-deficient ligand 2,6-ditrifluoromethyl benzoate facilitates Ce(IV)-mediated bond scission tert-butanol, generating methyl is subsequently captured by catalytic cycle to form C-CH3 bonds. Under mild conditions, this affords methylation sp3 carbons adjacent carbonyls sp2 centers, demonstrating broad functional group tolerance applicability late-stage functionalization bioactive molecules. Additionally, trideuteromethylative coupling can be facilely achieved using commercial tert-butanol-d10. This approach circumvents need traditional tert-butoxy precursors, such peroxides, while strategically pathway favor β-scission suppress unwanted formation solution. Mechanistic studies reveal plays crucial role facilitating generation, supporting concerted Ce-OR β-C-C homolysis mechanism, further evidenced modulation regioselectivity alkoxy radical-mediated β-scission.

Language: Английский

Citations

Catalytic undirected methylation of unactivated C(sp3)−H bonds suitable for complex molecules DOI

Jin-Fay Tan, Yi Cheng Kang, John F. Hartwig

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: Sept. 27, 2024

Language: Английский

Citations

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

Peng Wu,

Gabriel Goujon,

Shulei Pan

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(51)

Published: Sept. 5, 2024

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

Language: Английский

Citations

Transition-Metal- and Photocatalyst-Free Photoinduced Formation of Carbon–Pnictogen (–N, –P) Bonds DOI

Rosalin Bhanja, Shyamal Kanti Bera, Prasenjit Mal

et al.

Synthesis, Journal Year: 2024, Volume and Issue: 56(17), P. 2627 - 2637

Published: April 2, 2024

Abstract Pnictogens, classified within group 15 elements, play a pivotal role in the constitution of diverse array drug molecules, natural products, and functional materials. Recent research has increasingly prioritized exploration mild conditions for synthesizing C–Pnictogen (C–N C–P) bonds, highlighting growing emphasis on efficient sustainable synthetic methodologies. This Short Review explores fundamental mechanisms, addresses constraints, assesses methodologies, underscoring potential photocatalyst- transition-metal-free photochemical reactions advancing sustainability. Divided into two segments, it encompasses recent advancements facilitating C–N C–P bond formation. 1 Introduction 2 Carbon–Nitrogen (C–N) Bond Formation 3 Carbon–Phosphorus (C–P) 4 Summary Outlook

Language: Английский

Citations

Ru(II)-Catalyzed Sustainable C–H Methylation of Indolines with Organoboranes in Ethanol DOI

Sumit Sharma,

Sachin,

Devesh Chandra

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 6, 2024

A sustainable protocol for Ru(II)-catalyzed regioselective C(sp

Language: Английский

Citations

Sustainable C–H Methylation Employing Dimethyl Carbonate DOI

Sangita Dattatray Shinde,

Garvita Narang,

Gargee Mahendra Mahajan

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(20), P. 14679 - 14694

Published: Oct. 4, 2024

The use of CO

Language: Английский

Citations

Base-mediated denitrative C3-alkylation of quinoxaline derivatives DOI

Vaibhav Ramachandra Pansare,

Nagaraju Barsu

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

A novel base-mediated C3-alkylation of quinoxalin-2(1 H )-one and its N -protected derivatives using inexpensive nitroalkanes has been developed. This method is scalable tolerates diverse functional groups supports bioactive compound synthesis.

Language: Английский

Citations

Photoredox-Catalyzed C–H Methylation of N-Heteroarenes Enabled by N,N-Dimethylethanolamine DOI

Jiayang Wang, Yun Wang, Wei-Yang Lin

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 21, 2024

A visible-light-driven radical C-H methylation of

Language: Английский

Citations