Photoredox-Catalyzed Aminolactonization of 2-Styrylbenzoic Acids with N-Aminopyridinium Salts to Access 4-Sulfonamino-3,4-dihydroisocoumarins DOI
Jinwei Yuan, Qiang Liu, Wei Lian

et al.

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

Published: Dec. 26, 2024

A photoredox-catalyzed aminolactonization of unsaturated carboxylic acids was achieved using N-aminopyridinium salts as the amino radical precursor. The transformation features mild conditions and a remarkably broad substrate scope, offering an efficient approach to construct wide range 4-sulfonamino 3,4-dihydroisocoumarins. Mechanistic studies indicate that reaction proceeds via distinctive salt-promoted electrophilic amination 2-styrylbenzoic acids.

Language: Английский

Photoredox-Catalyzed Three-Component Sulfonaminoalkynylation of Alkenes via a Radial/Polar Crossover DOI

Lixian Shen,

Jie Liu, Peng Xue

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 90(4), P. 1656 - 1662

Published: Jan. 21, 2025

We report a photoredox-catalyzed three-component sulfonaminoalkynylation of alkenes with N-aminopyridine salts and potassium alkynyltrifluoroborate salts. This aminoalkylation reaction underwent radial/polar crossover mechanism, which was distinguished from the previous reports. A variety β-alkynylated sulfonamides were obtained in moderate to excellent yields. The versatility this method further evidenced by its successful application modifying biological molecules advanced stages development.

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
Access to tetrahydrocarbazoles via a photocatalyzed cascade decarboxylation/addition/cyclization reaction DOI
Shuai Han, Zhang Chen, Yu Guo

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(23), P. 6694 - 6699

Published: Jan. 1, 2024

An efficient photocatalyzed decarboxylative coupling of indolepropionic acid NHPI esters with α,β-unsaturated carbonyl compounds has been developed, which provided structurally diverse tetrahydrocarbozles in moderate to good yields.

Language: Английский

Citations

1
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
Photoredox-Catalyzed Aminolactonization of 2-Styrylbenzoic Acids with N-Aminopyridinium Salts to Access 4-Sulfonamino-3,4-dihydroisocoumarins DOI
Jinwei Yuan, Qiang Liu, Wei Lian

et al.

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

Published: Dec. 26, 2024

A photoredox-catalyzed aminolactonization of unsaturated carboxylic acids was achieved using N-aminopyridinium salts as the amino radical precursor. The transformation features mild conditions and a remarkably broad substrate scope, offering an efficient approach to construct wide range 4-sulfonamino 3,4-dihydroisocoumarins. Mechanistic studies indicate that reaction proceeds via distinctive salt-promoted electrophilic amination 2-styrylbenzoic acids.

Language: Английский

Citations

0