Sulfonyl Radical-Induced Regioselective Cyclization of Enamide–Olefin To Form Sulfonylated 6–7-Membered Cyclic Enamines DOI
Ran Ding, Gang Dong, Xu Tang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(21), P. 15733 - 15738

Published: Oct. 16, 2024

Remarkable progress has been made in the radical cascade cyclization of heteroaryl- or aryl-tethered alkenes to construct benzene-fused frameworks via cracking aryl C–H bonds. In contrast, linear dienes through vinyl bonds nonbenzene-fused ring with endocyclic double significantly lagged behind, and major advances have largely restricted generation 5-membered heterocycles, such as pyrrolinones. Herein, we report silver-mediated regioselective sulfonylation-cyclization sodium sulfinates form sulfonylated 6- 7-membered cyclic enamines.

Language: Английский

Iron(III)-Mediated Nucleophilic Cascade Cyclization of Tertiary Enamides with Diselenides for the Construction of 3-Seleno-2-pyridones DOI
Xin‐Ming Xu, Jiping Wang, Xiaoxu Chen

et al.

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

Published: Jan. 12, 2025

An iron(III)-mediated nucleophilic cascade cyclization of N-propiolyl enamides with various diselenides was developed, which provides an efficient way to construct seleno-heterocycles. A mechanism study shows that the process involves selective addition C≡C bond generating a seleniranium ion, followed by intramolecular attack enaminic carbon tertiary enamide. Utilizing this protocol, variety 3-seleno-2-pyridones were successfully synthesized featuring good functional group compatibility and simple operation.

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
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 Three-Component Radical Sulfonarylation of Alkenes: Preparation of γ-Keto-Sulfone-Substituted Oxindoles DOI
Fei Chen,

Jun-Ya Guo,

Yunhong Jia

et al.

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

Published: March 16, 2025

A photocatalytic radical sulfonarylation of N-arylacrylamides via a three-component cascade cyclopropyl alcohol ring opening/sulfur dioxide insertion/sulfonyl addition/cyclization sequence has been developed. This method employs alcohols as the precursors β-carbonyl alkyl radicals and Na2S2O5 cheap source sulfur dioxide. By using this procedure, wide variety γ-keto-sulfone-substituted oxindoles were facilely synthesized.

Language: Английский

Citations

0
Reactions of alkynes with C–S bond formation: recent developments DOI

Yuemei Xu,

S. ZHANG, Dayun Huang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(32), P. 6443 - 6484

Published: Jan. 1, 2024

Alkynes are important in organic synthesis. This review mainly focuses on the recent advances (2013–2023) alkynes with C–S bond formation, based more than 30 kinds of sulfur reagents.

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
Hydrothermal precipitation of copper from leaching solutions of metallurgical dusts DOI Creative Commons

A. A. Kovyazin,

К. Л. Тимофеев, G. I. Maltsev

et al.

iPolytech Journal, Journal Year: 2024, Volume and Issue: 28(3), P. 547 - 561

Published: Oct. 5, 2024

In this work, we aim to establish the main regularities of hydrothermal precipitation copper from previously unstudied sulfuric-nitric acid and sulfate solutions atmospheric autoclave processing metallurgical dusts. Pyrite was used as a sulfidizer. The elemental composition products determined by X-ray fluorescence, inductively coupled plasma atomic emission spectrometry, absorption analysis. It found that proposed technology enables its recovery at level more than 95%. For with high arsenic concentration, two-stage scheme oxidation-hydrothermal treatment following parameters proposed: temperature 180°С, duration 2 h, oxygen consumption 0.026 dm 3 /g pyrite (for 1st stage), 200°С h 2nd stage). Extraction in cake amounted 95.4% (in form Cu S) 91.4% FeAsO 4 ), which allowed further separation these metals flotation. An Cu–Zn–Fe–As–NO solution presence 180–220°С produced activation energy values (kJ/mol) corresponding kinetic regime calculated two methods: 64.6 conventional method 60.5 shrinking core model. CuSO –H SO –FeS O CuNO systems were also determined. Flotation enrichment shown result degree As separation, amounting ˃ 95% ˂ 5%. Precious contained are transferred flotation concentrate 92.7% (Au) 96.5% (Ag). resulting comprised (%): 12 Cu; 37 Fe; 38 S; 13 other elements. is that, order obtain product required content copper, should be separated into concentrates followed an additional primary alkaline medium lime. Hence, our study has established

Language: Английский

Citations

1
Sulfonyl Radical-Induced Regioselective Cyclization of Enamide–Olefin To Form Sulfonylated 6–7-Membered Cyclic Enamines DOI
Ran Ding, Gang Dong, Xu Tang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(21), P. 15733 - 15738

Published: Oct. 16, 2024

Remarkable progress has been made in the radical cascade cyclization of heteroaryl- or aryl-tethered alkenes to construct benzene-fused frameworks via cracking aryl C–H bonds. In contrast, linear dienes through vinyl bonds nonbenzene-fused ring with endocyclic double significantly lagged behind, and major advances have largely restricted generation 5-membered heterocycles, such as pyrrolinones. Herein, we report silver-mediated regioselective sulfonylation-cyclization sodium sulfinates form sulfonylated 6- 7-membered cyclic enamines.

Language: Английский

Citations

0