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

Farrukh Sajjad,

Chang Lu,

Tie‐Gen Chen

и другие.

European Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Дек. 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.

Язык: Английский

Photoredox-Catalyzed Alkylamination of Alkenes via Oxidative Radical-Polar Crossover and Site-Selective 1,5-Hydrogen Atom Transfer DOI
Tianle Huang, Jianghong Liu,

Zhen-Ye Wu

и другие.

Organic Letters, Год журнала: 2024, Номер 26(32), С. 6847 - 6852

Опубликована: Авг. 7, 2024

We reported the visible-light-mediated photoredox-catalyzed oxidative radical-polar crossover and 1,5-hydrogen atom transfer combined site-selective remote C(sp

Язык: Английский

Процитировано

4

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

Ting Xiong,

Qilong Chen, Ziyan Zhang

и другие.

ACS Catalysis, Год журнала: 2024, Номер 14(16), С. 12082 - 12092

Опубликована: Июль 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.

Язык: Английский

Процитировано

3

Iron(II)‐Catalyzed 1,2‐Diamination of Styrenes Installing a Terminal NH2 Group Alongside Unprotected Amines DOI Creative Commons
Valentyn Pozhydaiev,

Antonio Paparesta,

Joseph Moran

и другие.

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(45)

Опубликована: Июль 17, 2024

1,2-Diamination of alkenes represents an attractive way to generate differentiated vicinal diamines, which are prevalent motifs in biologically active compounds and catalysts. However, existing methods usually limited scope produce diamines where one or both nitrogens protected, adding synthetic steps for deprotection further N-functionalization reach a desired target. Furthermore, the range amino groups that can be introduced at internal position is fairly limited. Here we describe 1,2-diamination styrenes directly installs free group terminal wide variety unprotected nitrogen nucleophiles (primary secondary alkyl aromatic amines, sulfoximines, N-heterocycles, ammonia surrogate) position. Two complementary sets conditions encompass electronically activated deactivated with diverse substitution patterns functional groups. Moreover, this strategy extended 1,2-aminothiolation styrenes.

Язык: Английский

Процитировано

1

Remote Radical Azidation of Unactivated C(sp3)–H Bonds in Sulfamoyl Azides DOI
Jiawei Li,

Sishi Zhong,

Pan Zhou

и другие.

Organic Letters, Год журнала: 2024, Номер 26(17), С. 3519 - 3523

Опубликована: Апрель 23, 2024

An efficient method for remote radical C(sp3)–H azidation at unactivated sites is described. C–H functionalization proceeds via intramolecular 1,5-hydrogen atom transfer to N-centered radicals that are generated azido group and/or fragmentation. The readily installed sulfamoyl azide serves as both an amidyl precursor and source. This reaction features excellent site selectivity tertiary, secondary, primary, benzylic bonds exhibits broad functional compatibility.

Язык: Английский

Процитировано

0

Iron(II)‐Catalyzed 1,2‐Diamination of Styrenes Installing a Terminal NH2 Group Alongside Unprotected Amines DOI Creative Commons
Valentyn Pozhydaiev,

Antonio Paparesta,

Joseph Moran

и другие.

Angewandte Chemie, Год журнала: 2024, Номер 136(45)

Опубликована: Июль 17, 2024

Abstract 1,2‐Diamination of alkenes represents an attractive way to generate differentiated vicinal diamines, which are prevalent motifs in biologically active compounds and catalysts. However, existing methods usually limited scope produce diamines where one or both nitrogens protected, adding synthetic steps for deprotection further N‐functionalization reach a desired target. Furthermore, the range amino groups that can be introduced at internal position is fairly limited. Here we describe 1,2‐diamination styrenes directly installs free group terminal wide variety unprotected nitrogen nucleophiles (primary secondary alkyl aromatic amines, sulfoximines, N ‐heterocycles, ammonia surrogate) position. Two complementary sets conditions encompass electronically activated deactivated with diverse substitution patterns functional groups. Moreover, this strategy extended 1,2‐aminothiolation styrenes.

Язык: Английский

Процитировано

0

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

Farrukh Sajjad,

Chang Lu,

Tie‐Gen Chen

и другие.

European Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Дек. 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.

Язык: Английский

Процитировано

0