Advances in C‐N bond Formation via N‐centered Radicals from N‐Aminopyridinium Reagents DOI

Farrukh Sajjad,

Chang Lu,

Tie‐Gen Chen

et al.

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

Published: Dec. 12, 2024

Abstract Nitrogen‐centered radicals (NCRs) have gained significant attention due to their high reactivity, which facilitates many useful and challenging transformations, particularly in the formation of C−N bonds. In this regard, N ‐aminopridinium reagents are easily accessible substrates that readily generate ‐centered radicals, can be trapped by arenes, olefins, alkynes even alkanes under visible light irradiation. recent years, amination strategies involving ‐aminopyridinium salts grown remarkably attracted considerable interest within synthetic community. This review comprehensively includes all advances bond construction via derived from substrates.

Language: Английский

5-Aminopyrazole Dimerization: Cu-Promoted Switchable Synthesis of Pyrazole-Fused Pyridazines and Pyrazines via Direct Coupling of C-H/N-H, C-H/C-H, and N-H/N-H Bonds DOI Creative Commons

Yi-Xin Chai,

Junjie Ren,

Yi‐Ming Li

et al.

Molecules, Journal Year: 2025, Volume and Issue: 30(2), P. 381 - 381

Published: Jan. 17, 2025

A Cu-promoted highly chemoselective dimerization of 5-aminopyrazoles to produce pyrazole-fused pyridazines and pyrazines is reported. The protocol generates switchable products via the direct coupling C-H/N-H, C-H/C-H N-H/N-H bonds, with merits broad substrate scope high functional group compatibility. Gram-scale experiments demonstrated potential applications this reaction. Moreover, preliminary fluorescence results uncovered that dipyrazole-fused may have some in materials chemistry.

Language: Английский

Citations

0
Difluorocarbene-Enabled Dehydration of Primary Amides To Access Nitriles DOI

Bofan Feng,

Huosheng Guo,

Xiaosha Wang

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 16, 2025

A cost-effective and environmentally friendly method for the direct conversion of primary amides to nitriles was developed using commercially available non-toxic ethyl bromodifluoroacetate as a difluorocarbene precursor under metal-free ligand-free conditions. The reaction features high yields tolerates various sensitive moieties, including alkyl, alkenyl, ether, sulfone, sulfoxide, heteroaryl, chloro, bromo, iodo, hydroxyl, nitro, cyano groups, late-stage modification complex molecules is also feasible. Moreover, present effective on large scales, showing potential industrial application.

Language: Английский

Citations

0
Controllable Radical Reactions of 1,3-Dienes with Light DOI

Shiwei Lü,

Jin Xie

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 7749 - 7779

Published: April 25, 2025

Language: Английский

Citations

0
Direct Fluorosulfonamidation of (Hetero)arenes and Alkenes with Photoredox-Active Fluorosulfamoyl Radical Reagents DOI

Ting Xiong,

Qilong Chen, Ziyan Zhang

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(16), P. 12082 - 12092

Published: July 29, 2024

Sulfur(VI) fluoride exchange (SuFEx) is a second-generation click chemistry reaction that relies on the unique reactivities of SVI–F bonds. The development efficient methods for incorporating S(VI)–F motif into molecules great significance. Sulfamoyl fluorides (R1R2NSO2F), serving as versatile SuFExable hubs, are typically synthesized by using "+SO2F" reagents to establish N-SO2F In this study, we report N-fluorosulfamoyl pyridium salts (NFSAPs) radical fluorosulfonamidation readily accessible and bench-stable. By employing NFSAPs essential fluorosulfamoyl (•NSO2F) precursors, direct installation NSO2F group onto (hetero)arenes alkenes achieved through distinct C–N bond formation reactions. This platform facilitates collective synthesis highly functionalized N-aryl, N-alkyl, N-alkenyl sulfamoyl (R1R2NSO2F) under mild photocatalytic conditions has been applied in late-stage functionalization pharmaceuticals peptides.

Language: Английский

Citations

3
Visible light promoted synthesis of allenes DOI
Jitender Singh,

Barakha Saxena,

Anuj Sharma

et al.

Catalysis Science & Technology, Journal Year: 2024, Volume and Issue: 14(18), P. 5143 - 5160

Published: Jan. 1, 2024

This review article summarizes the visible light mediated synthesis of allenes from substrates like 1,3-enynes, propargylic carbonates, homopropargylic alcohols, oxalates, alkynyl diazo compounds, and terminal aziridines.

Language: Английский

Citations

2
Metallaphotoredox Synthesis of Axially Chiral Tetrasubstituted Allenes through Regio- and Enantioselective 1,4-Carbocyanation of 1,3-Enynes DOI

Keyi Peng,

Ya-Sheng Cao,

Quanyuan Wang

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(18), P. 14048 - 14057

Published: Sept. 10, 2024

Language: Английский

Citations

2
Photoreductive 1,4-Dicarbofunctionalization of 1,3-Enynes with Organoiodides and Cyanoarenes via Halogen-Atom Transfer DOI

Liangfeng Yang,

Liang Zeng,

Yilin Liu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(36), P. 7661 - 7666

Published: Aug. 28, 2024

A photoreductive halogen-atom transfer (XAT) strategy for 1,4-dicarbofunctionalization of 1,3-enynes with organoiodides and cyanoarenes is disclosed, enabling access to functionalized allenes in a highly regio-, chemo-, stereoselective manner. Upon the photoredox catalysis activation Et

Language: Английский

Citations

0
Advances in C‐N bond Formation via N‐centered Radicals from N‐Aminopyridinium Reagents DOI

Farrukh Sajjad,

Chang Lu,

Tie‐Gen Chen

et al.

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

Published: Dec. 12, 2024

Abstract Nitrogen‐centered radicals (NCRs) have gained significant attention due to their high reactivity, which facilitates many useful and challenging transformations, particularly in the formation of C−N bonds. In this regard, N ‐aminopridinium reagents are easily accessible substrates that readily generate ‐centered radicals, can be trapped by arenes, olefins, alkynes even alkanes under visible light irradiation. recent years, amination strategies involving ‐aminopyridinium salts grown remarkably attracted considerable interest within synthetic community. This review comprehensively includes all advances bond construction via derived from substrates.

Language: Английский

Citations

0