Photocatalytic Regioselective Tandem Cyclization Protocol to Trifluoromethylated Pyrrolidones DOI Open Access
Panpan Wang, Yuting Leng,

Kaixia Sui

et al.

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

Published: Oct. 21, 2024

Abstract A new environmentally friendly and efficient strategy for preparing trifluoromethylated pyrrolidones has been developed. The process involves using visible light to induce radical cyclization of 1,5‐dienes with CF 3 SO 2 Na, resulting in excellent regioselectivity. This method uses less expensive easy‐to‐store trifluoromethylation reagents, making it an attractive option. Additionally, the can be easily modified preliminary mechanistic studies have presented.

Language: Английский

Self‐ or Acridinium‐Catalyzed Electrophotosynthesis of Thiocyanato Heterocycles from Activated Alkenes DOI

Kaixing Gong,

Yingchun Ma,

Ping Yu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(10), P. 2352 - 2362

Published: April 5, 2024

Abstract While the emergence of electrophotochemistry provides opportunities, such a chemistry at this stage suffers from limited reaction types and high photocatalyst loadings. A self‐catalyzed electrophotosynthesis as well one with low loading is presented. These external‐oxidant‐free cyclizations are enabling applicable to range activated alkenes, affording diverse array thiocyanato heterocycles including 4‐pyrrolin‐2‐ones, isoquinoline‐1,3‐diones, indolo[2,1‐ ]isoquinolin‐6(5 H )‐ones, benzoimidazo[2,1‐ )‐ones indolin‐2‐ones, protocols amenable late‐stage diversification complex molecular architectures gram‐scale syntheses. Sunlight could serve light source, be conducted in an all‐solar‐driven mode using commercially available photovoltaic panel produce electricity.

Language: Английский

Citations

9

Recent advances on electrochemical generation of sulfonyl radical triggered cyclization of alkene/alkynes DOI

Jiaqing Shao,

Jiang Liu, Haibo Mei

et al.

Tetrahedron, Journal Year: 2025, Volume and Issue: 173, P. 134467 - 134467

Published: Jan. 12, 2025

Language: Английский

Citations

1

Divergent Synthesis of Polysubstituted 1,2-Dihydropyridines and Pyridines through Manganese-Mediated Radical Cascade Cyclization of Tertiary Enamides DOI
Xiaoxu Chen, Sen Chen, Jiping Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 28, 2025

A Mn(III)-mediated radical cascade cyclization of N-propargyl enamides with sodium sulfinates was developed. Mechanistic studies indicated that this process is mainly composed the chemoselective addition sulfonyl to C≡C bond and regioselective intramolecular 6-endo-trig cyclization. This protocol provided a powerful method for divergent synthesis diverse polysubstituted meta-sulfonylpyridines or 1,2-dihydropyridines just by varying solvent temperature featuring good functional group compatibility simple operation.

Language: Английский

Citations

1

Electrophotocatalysis Versus Indirect Electrolysis: Electrochemical Selenocyclization of 3‐Aza‐1,5‐dienes Facilitated by Energy Transfer, Direct Photolysis or N‐Hydroxyphthalimide DOI

Dongyin Wang,

Li Zeng, Jifu Shi

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(36)

Published: April 23, 2024

Three hybrid electrochemical protocols, which involve the energy transfer, direct photolysis and N-hydroxyphthalimide catalyst, respectively, are presented for selenylation/cyclization of fragile substrates 3-aza-1,5-dienes with diorganyl diselenides to afford 3-selenomethyl-4-pyrrolin-2-ones. The two electrophotocatalytic reactions indirect electrolysis one both regioselective external-oxidant- transition-metal-free, associated a broad substrate scope high Se-economy, all three methods amenable gram-scale syntheses, late-stage functionalizations, sunlight-induced experiments all-solar-driven syntheses.

Language: Английский

Citations

6

Manganese(III)-Mediated Selective Cascade Phosphorylation-Cyclization of Tertiary Enamides for the Synthesis of Multi-Substituted 3-Phosphorylpyridines DOI
Xin‐Ming Xu, Sen Chen, Qian Liu

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 14, 2025

A novel regioselective manganese(III)-mediated radical cascade cyclization of N-propargyl enamides with various H-phosphine oxides, H-phosphinates and H-phosphonates was developed. Mechanistic studies show that the reaction is mainly composed selective addition phosphonyl to C≡C bond intramolecular 6-endo-trig vinyl radical. Utilizing this protocol, we successfully synthesized a diverse range 3-phosphorylpyridines in high efficiency good functional group compatibility simple operation.

Language: Английский

Citations

0

Synthesis of meta-Sulfonylpyridines via Copper(II)-Catalyzed Cascade Sulfonylation/Cyclization/Aromatization of Tertiary Enamides with Sulfonylhydrazides DOI
Xin‐Ming Xu, Jiping Wang, Xiaoxu Chen

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 5, 2025

A copper(II)-catalyzed radical cascade reaction of N-propargyl enamides with sulfonyl hydrazides was developed, which provided an unprecedented method for the direct synthesis meta-sulfonylpyridines in high efficiency good functional group compatibility and simple operation. Mechanistic studies indicated that this tandem process might be composed addition, intramolecular cyclization oxidative aromatization.

Language: Английский

Citations

0

Photocatalytic Regioselective Alkoxycarbonylation/Cyclization of 3-Aza-1,5-dienes: Access to Ester-Containing Pyrrolin-2-ones DOI

Yuping Xiong,

Zhipeng Zong,

Wenlin Xie

et al.

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

Published: March 13, 2025

A direct alkoxycarbonyl radical-induced cascade reaction of 3-aza-1,5-dienes with alkyl chlorooxoacetates is reported. With this approach, an extensive range ester-containing pyrrolin-2-ones are synthesized through photocatalyzed alkoxycarbonylation/cyclization under mild conditions. Moreover, dehydrogenative aromatization can proceed the same photocatalytic system.

Language: Английский

Citations

0

Photo- and electro-induced perfluoroalkylation/cyclization of o-hydroxyaryl enaminones: Synthesis of perfluoroalkyl chromones DOI Creative Commons

Shengjie Song,

Wenjian Wang,

Jun Sun

et al.

Green Synthesis and Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: March 1, 2024

A practical, metal-, and additive-free strategy for photo- electro-induced perfluoroalkylation/cyclization of o-hydroxyaryl enaminones with sodium perfluoroalkanesulfinates under mild conditions has been developed. Various fluoroalkyl chromones were efficiently assembled in moderate to good yields. The scalability this protocol the assembling diverse nitrogen-containing heterocycles from late-stage transformations greatly broaden practical applications developed protocol.

Language: Английский

Citations

2

Electroreductive Carboxylation of Benzylphosphonium salts with CO2 Through the Cleavage of the C(sp3)-P Bond DOI

Fen Han,

Fenfen Xie,

Mengyun Yin

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(28), P. 5724 - 5728

Published: Jan. 1, 2024

Herein, a novel electroreductive carboxylation of benzylphosphine salts with CO 2 through cleavage the C(sp 3 )-P bond was reported under conditions without redox reagents and noble metal catalysts.

Language: Английский

Citations

2

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

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(20), P. 5784 - 5790

Published: Jan. 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.

Language: Английский

Citations

2