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

Photoredox Catalysis for the Synthesis of N‐CF2H Compounds Using 1‐((N‐(difluoromethyl)‐4‐methylphenyl)‐sulfonamido)pyridin‐1‐ium Trifluoromethanesulfonate DOI Creative Commons
Daniel Lin, Juan Pablo de los Rios, G. K. Surya Prakash

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(30)

Published: May 26, 2023

Abstract N ‐(difluoromethyl)amino (−NCF 2 H) compounds are of great interest given their unique and underexplored physiochemical properties. The lack structural diversity in NCF H is likely due part to the shortage protocols for efficient installation. Presented herein a new shelf‐stable pyridinium reagent that enables direct installation ‐(difluoromethyl)sulfonamide moiety [N(Ts)CF H)] onto (hetero)arenes alkenes diversification aryl alkyl compounds. described protocol utilizes blue light photoredox catalysis displays broad functional group tolerance with excellent chemoselectivity. Additional transformations applicability towards continuous flow also demonstrated.

Language: Английский

Citations

15
Self-catalytic photochemical three-component reaction for the synthesis of multifunctional 3,3-disubstituted oxindoles DOI
Kai Zheng,

Keyuan Liang,

Jiannan Zhu

et al.

Molecular Catalysis, Journal Year: 2024, Volume and Issue: 565, P. 114379 - 114379

Published: July 9, 2024

Language: Английский

Citations

5
Coupling-Spirocyclization Cascade of Tryptamine-Derived Isocyanides with Iodonium Ylides and Despirocyclization Reactions DOI

Luo-Rong Yuan,

Shun‐Jun Ji, Xiaoping Xu

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(43), P. 7858 - 7862

Published: Oct. 20, 2023

A cobalt(II)-catalyzed coupling-cyclization cascade reaction between tryptamine-derived isocyanides and iodonium ylides is investigated, which allowed for the synthesis of different types spiroindoline compounds by variation substituents at N1- C2-positions in indole skeleton. More interesting that products could undergo despirocyclization presence amines, enabling efficient construction enamine compounds.

Language: Английский

Citations

7
Practical conversion of gem-difluorocyclopropenes for the chemodivergent assembly of fluorinated heterocyclic frameworks DOI

Dongping Pan,

Fu‐Xiaomin Liu,

Zhongyi Zeng

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(24), P. 10630 - 10637

Published: Jan. 1, 2023

A green method has been established by employing gem -difluorocyclopropylenes as versatile building blocks, leading to the chemodivergent formation of several fluorinated structural motifs including cyclopropapyrazolopyridines, indolizines etc .

Language: Английский

Citations

6
SO2ClF-promoted chlorination-oxidation of 2-methylindoles: a one-step synthetic method to access 2,3-difunctionalized indoles DOI
Yu Zheng,

Tianting Ma,

Bingcong Liu

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(16), P. 4100 - 4104

Published: Jan. 1, 2023

We developed a convenient and one-step methodology for the synthesis of 3-chloro-2-formylindoles from readily available 2-methylindoles SO 2 ClF.

Language: Английский

Citations

4
Photoredox Catalysis for the Synthesis of N‐CF2H Compounds Using 1‐((N‐(difluoromethyl)‐4‐methylphenyl)‐sulfonamido)pyridin‐1‐ium Trifluoromethanesulfonate DOI Creative Commons
Daniel Lin, Juan Pablo de los Rios, G. K. Surya Prakash

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(30)

Published: May 26, 2023

Abstract N ‐(difluoromethyl)amino (−NCF 2 H) compounds are of great interest given their unique and underexplored physiochemical properties. The lack structural diversity in NCF H is likely due part to the shortage protocols for efficient installation. Presented herein a new shelf‐stable pyridinium reagent that enables direct installation ‐(difluoromethyl)sulfonamide moiety [N(Ts)CF H)] onto (hetero)arenes alkenes diversification aryl alkyl compounds. described protocol utilizes blue light photoredox catalysis displays broad functional group tolerance with excellent chemoselectivity. Additional transformations applicability towards continuous flow also demonstrated.

Language: Английский

Citations

3
Atroposelective Amination of Indoles via Chiral Center Induced Chiral Axis Formation DOI Creative Commons
Yong Wang,

Jingxue Yan,

Yiqing Jiang

et al.

Molecules, Journal Year: 2022, Volume and Issue: 27(24), P. 9008 - 9008

Published: Dec. 17, 2022

The construction of an N-C chiral axis for N-aryl indole derivatives is meaningful as they widely exist in functionalized molecules. This work provides a novel method this purpose via amination amino acid at the C2 position and center induced formation. protocol transformation easily accessible, not requiring metal or organic catalyst, endowing with great potential indoles.

Language: Английский

Citations

5
Design of N–N ylide bond-based high energy density materials: a theoretical survey DOI Creative Commons
Jingfan Xin, Xiaoxu Bo,

Wenmin Xiao

et al.

RSC Advances, Journal Year: 2024, Volume and Issue: 14(7), P. 4456 - 4460

Published: Jan. 1, 2024

Our work, for the first time, describes possibility of designing structures with a fourth type homonuclear N–N bond (besides >NN<, –NN–, and NN) to serve as energetic materials.

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