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

Electrochemical Trifluoromethylation and Sulfonylation of N-Allylamides: Synthesis of Oxazoline Derivatives DOI
Shujun Chen, Weiqiang Zhong, Jing‐Mei Huang

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(17), С. 12630 - 12640

Опубликована: Авг. 14, 2023

We report a new method for the synthesis of trifluoromethylated and sulfonylated oxazolines by electrochemical radical cascade cyclizations N-allylamides with sodium trifluoromethanesulfinate or sulfonylhydrazines. This protocol provides green useful strategy to synthesize broad substrate scope under ambient conditions.

Язык: Английский

Процитировано

7

Photoredox‐Catalyzed Metal‐Free Regio‐ & Stereoselective C(sp2)–H Amination of Enamides with N‐Aminopyridium Salts DOI

Zheng‐Bao Qin,

Kun Ni,

Wang Li

и другие.

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(18), С. 2235 - 2242

Опубликована: Май 11, 2024

Comprehensive Summary A visible‐light‐induced photoredox‐catalyzed regioselective and stereoselective C(sp 2 )–H amination of enamides with bench‐stable easily accessible N ‐aminopyridium salts is developed, affording synthetically biologically prominent vicinal 1,2‐diamine scaffolds broad substrate scope excellent functional group compatibility. The transformation proceeded through a radical pathway involving the Giese addition relatively electrophilic ‐centered sulfonamidyl species to nucleophilic β‐olefinic position followed by ensuing single electron oxidation β‐H elimination, delivering geometrically‐defined Z ‐configured β‐sulfonamidylated enamides. operational simplicity, environmental friendliness cost efficiency this methodology allowed it pave new avenue enrich arsenal crucial functionalized their related derivatives.

Язык: Английский

Процитировано

2

Regioselective tandem sulfonylation/cyclization of unsaturated N-substituted enamides with sulfonyl chlorides by copper catalysis DOI
Ran Ding, Tao Wu, Tao Ma

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(20), С. 5784 - 5790

Опубликована: Янв. 1, 2024

The radical cascade cyclization of vinyl-tethered alkenes has become a promising tool for rapidly assembling nonbenzene-fused cyclic skeletons via the cracking alkenyl C–H bonds, but this approach been limited to generate five-membered rings.

Язык: Английский

Процитировано

2

Visible‐Light‐Driven Sulfonamidation of Arylazo Sulfonesthrough One‐Pot Multicomponent Reaction DOI
Truong Giang Luu, Hee‐Kwon Kim

Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 12(8)

Опубликована: Июль 8, 2023

Abstract Sulfonamide is one of the most important structures in organic chemistry due to its frequent appearance natural products as well pharmaceuticals. This study reports a visible‐light‐promoted strategy for synthesis sulfonamides from arylazo sulfones. One‐pot tri‐component reactions were conducted using sulfones, DABSO, and amines presence CuBr 2 coupling catalyst under irradiation with blue LEDs prepare various good yields mild conditions. method could be used effectively produce variety useful sulfonamides.

Язык: Английский

Процитировано

5

N-Chlorosulfonyl carbamate-enabled, photoinduced amidation of quinoxalin-2(1H)-ones DOI

Chu‐Ping Yuan,

Zhenzhen Xie, Yu Zheng

и другие.

Chemical Communications, Год журнала: 2023, Номер 59(67), С. 10125 - 10128

Опубликована: Янв. 1, 2023

Reported herein is the design and development of a new photo-induced amidation protocol with readily available N-chlorosulfonyl carbamate as an effective amidyl-radical precursor, which could be prepared from commercial low-cost chlorosulfonyl isocyanate (CSI) alcohol feedstocks. The synthetic potency this developed was well demonstrated by direct various quinoxalin-2(1H)-ones. further streamlined implementing one-pot/two-step/three-component process CSI, alcohol, quinoxalin-2(1H)-one, significantly improved reaction efficiency. This methodology offers intriguing opportunity for rapid expansion nitrogen-containing molecular complexity, thus inspiring comprehensive exploration mode CSI reagent.

Язык: Английский

Процитировано

5

Photo‐Induced Oxyamination of Alkenyl Acids towards Amino Lactones DOI
Changduo Pan, Dongdong Chen,

Miao Zeng

и другие.

European Journal of Organic Chemistry, Год журнала: 2023, Номер 26(46)

Опубликована: Окт. 30, 2023

Abstract Photo‐induced sulfonylamidation/lactonization of alkenyl acids with N ‐sulfonylaminopyridinium salts is demonstrated to access sulfonamidylated lactones under mild and metal‐free conditions. This reaction features a broad substrate scope, good functional group tolerance easy operation, providing simple efficient protocol for the synthesis lactones.

Язык: Английский

Процитировано

4

Divergent Assembly of Functionalized Pyrazolo[1,5‐a]pyridine Derivatives via [3+2] Cyclization of N‐Aminopyridinium Salts with Various Unsaturated Hydrocarbons DOI
Xiang Liu, Shaohong Ma,

Shi Yan

и другие.

Chinese Journal of Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Сен. 10, 2024

Comprehensive Summary Two reaction modes for metal‐free [3 + 2] cyclization of N ‐aminopyridinium derivatives with β ‐alkoxyvinyl trifluoromethylketones have been described through selective C—O or C—O/C—C bond cleavage. This strategy can also be extended to the enaminones and bromoalkynes. A broad range ‐aminopyridinium, ‐aminoquinolinium, ‐aminoisoquinolinium salts are well tolerated, enabling divergent synthesis trifluoroacylated, non‐substituted, acylated, brominated pyrazolo[1,5‐ a ]pyridine (62 examples).

Язык: Английский

Процитировано

1

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

и другие.

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

Опубликована: Дек. 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.

Язык: Английский

Процитировано

1

Electrochemical Benzylic C–H Amination via N-Aminopyridinium DOI
Jingwei Liu,

Jinyao Du,

Lin‐Bao Zhang

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(9), С. 6465 - 6473

Опубликована: Апрель 22, 2024

An electrochemical protocol for benzylic C(sp3)–H aminopyridylation via direct C–H/N–H cross-coupling of alkylarenes with N-aminopyridinium triflate has been developed. This method features excellent site-selectivity, broad substrate scope, redox reagent-free and facile scalability. The generated benzylaminopyridiniums can be readily converted to benzylamines electroreductive N–N bond cleavage.

Язык: Английский

Процитировано

1

Silver-mediated radical cascade cyclization of N-allylamides with sodium sulfinates to access sulfonated oxazolines DOI
Zhichao Chen,

Mu He,

Hongmei Zheng

и другие.

New Journal of Chemistry, Год журнала: 2023, Номер 47(26), С. 12487 - 12491

Опубликована: Янв. 1, 2023

A facile and practical silver-mediated radical cascade cyclization of N -allylamides with sodium sulfinates is developed, giving a series sulfonated oxazolines in moderate to good yields.

Язык: Английский

Процитировано

1