Electrochemical Synthesis of 3-(Sulfonyl)quinol-4-ones from o-Alkynyl-N-(formyl)anilides and Sulfinates DOI

Vladimir L. Bondarev,

Alexey А. Festa, Olga А. Storozhenko

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 25, 2024

Electrolysis of o-alkynyl-N-(formyl)anilides and sodium sulfinates on graphite electrodes delivers biologically sound 3-(sulfonyl)quinol-4-ones with moderate to good yields. The reaction is carried out in an undivided cell the presence silver(I) oxide potassium iodide or tetrafluoroborate as supporting electrolyte. tolerates variously substituted anilides well aryl alkyl sulfinates. transformation proceeds a domino sequence oxysulfonylation cyclocondensation steps.

Language: Английский

Electrochemical Sulfonylation/Cyclization of N-Alkenylacrylamides with Sodium Sulfinates or Sulfonyl Hydrazides DOI
Zhixian Yang,

Lu-Cai Ding,

Gui-Hong Yang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10660 - 10677

Published: July 18, 2024

Two general protocols for the regioselective electrochemically enabled sulfonylation cyclization of

Language: Английский

Citations

8

Regio- and Stereoselective Intermolecular 1,2-Difunctionalization of Terminal Alkynes: An Approach to Access (Z)-β-Amidovinylsulfones DOI
Rajesh Kumar,

Deepak Bhadoria,

Ruchir Kant

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(5), P. 2873 - 2884

Published: Feb. 14, 2024

We have developed the first I2/base-catalyzed regio- and stereoselective intermolecular β-amidosulfonylation of terminal alkynes using sodium sulfinates quinoxalinone derivatives. The present methodology is compatible with a broad spectrum various heterocyclic amides, alkynes, sulfinates. It provides rapid access to valuable (Z)-β-amidovinyl sulfones at mild conditions. Moreover, synthetic application this was demonstrated by late-stage functionalization numerous bioactive molecules.

Language: Английский

Citations

4

Sc(OTf)3-Catalyzed Diastereoselective Hydroxyheteroarylation of C–C σ-Bonds of Bicyclo[1.1.0]butanes with Azaheterocyclic N-Oxides DOI
Jiang Wang, Jiajia Liu, Chenwei Li

et al.

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

Published: March 22, 2025

A mild and atom-economical reaction for the Sc(OTf)3-catalyzed 1,3-hydroxyheteroarylation of bicyclo[1.1.0]butanes (BCBs) with azaaryl N-oxides via an unprecedented [4π+2σ] cycloaddition/ring-opening process is described. This transformation provides a novel strategy highly regio- diastereoselective preparation azaheterocycle-tethered 1,1,3,3-tetrasubstituted cyclobutane derivatives offers broad substrate scope high yields.

Language: Английский

Citations

0

Visible-light-induced photocatalyst-free cascade cyclization of 3-(2-(ethynyl)phenyl)quinazolinones to sulfonated quinolino[2,1-b]quinazolinones DOI

Fan‐Lin Zeng,

Lili Wang,

Yuxin Luo

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(56), P. 7228 - 7231

Published: Jan. 1, 2024

A visible-light-induced K 2 S O 8 -promoted cascade sulfonation/cyclization reaction to afford a series of sulfonated quinolino[2,1- b ]quinazolinones has been developed under mild conditions.

Language: Английский

Citations

3

Progress in S–X Bond Formation by Halogen-Mediated Electrochemical Reactions DOI
Qingwen Gui, Juan Du,

Ya-Long Du

et al.

Synthesis, Journal Year: 2023, Volume and Issue: 55(18), P. 2799 - 2816

Published: May 19, 2023

Abstract Sulfur-containing compounds are very common and important heteroatom skeletons widely found in natural products, pharmaceuticals bioactive compounds. Moreover, the development of synthetic routes to organosulfur has attracted considerable attention due their wide range applications organic chemistry, pharmaceutical industry materials science. As one most powerful, green eco-friendly research areas, electrosynthesis, contrast conventional synthesis, can avoid use harmful stoichiometric external oxidants or reductants. Importantly, halide salts used as supporting electrolytes redox catalysts indirect electrosynthesis limitations imposed by high overpotentials direct electrosynthesis. In recent years, significant progress been made on halogen-mediated this review, scope, mechanisms electrochemical transformations sulfur-containing presented discussed. 1 Introduction 2 S–C Bond Formation 2.1 Organic Thiocyanates 2.2 Sulfonyl Compounds 2.3 Other Sulfides 3 S–X (X = N, O, S, P) Bonds 4 Conclusion Outlook

Language: Английский

Citations

4

Photocatalyst-free, visible-light-induced regio- and stereoselective synthesis of phosphorylated enamines from N-allenamides via [1,3]-sulfonyl shift at room temperature DOI Creative Commons
Jia‐Dong Guo, Feven-Alemu Korsaye, Dorian Schutz

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(43), P. 17962 - 17970

Published: Jan. 1, 2024

Herein, we report the first visible-light-induced strategy for rapid synthesis of densely functionalized α- and γ-phosphorylated β-sulfonyl enamines in a regio- stereoselective manner from N -sulfonyl allenamides H-phosphine oxides.

Language: Английский

Citations

1

Regio- and Stereoselective β-Sulfonylamination of Alkynes via Photosensitized Bifunctional N–S Bond Homolysis DOI

Tonglv Pu,

Si‐Hai Wu,

Liuyan Cai

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 4, 2024

Nitrogen central radicals (NCRs) are versatile synthetic intermediates for creating functional nitrogen-containing molecules. Herein, a photosensitized β-sulfonylamination of terminal alkynes as well acetylene has been established by employing N-sulfonyl heteroaromatics bifunctional reagents (BFRs) to efficiently deliver (E)-β-sulfonylvinylamines with excellent regio- and stereoselectivities. Mechanistic studies suggest base-accelerated energy transfer (EnT) photocatalysis involving aromatic NCR formation, radical addition alkynes, sulfonylation processes.

Language: Английский

Citations

1

Direct a-C(sp3)-H thioetheration/selenylation of nafimidone derivatives enabled by electrocatalysis DOI
Zhihao Wang, Jian Li,

Yumiao Liu

et al.

Molecular Catalysis, Journal Year: 2023, Volume and Issue: 540, P. 113038 - 113038

Published: March 4, 2023

Language: Английский

Citations

3

Electrochemical C(sp2)–H/N–H “formal” cross-dehydrogenative coupling of olefins with benzotriazoles for synthesis of N-vinyl benzotriazoles DOI

Jin-Feng Lv,

Yu‐Fang Tan, Ya‐Nan Zhao

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(42), P. 8488 - 8493

Published: Jan. 1, 2023

The paper details an electrochemical method that couples olefins with benzotriazoles to form C(sp2)-N bonds, enabling the synthesis of N-vinyl in moderate good yields. nBu4NI functions as both electrolyte and iodine mediator, does not require oxidants or metals. It is a highly atom-economical clean reaction, hydrogen sole byproduct.

Language: Английский

Citations

3

Visible Light Promoted Coupling Reaction of Alkynyl Iodide and Sodium Sulphinate without Photocatalyst DOI
Wenwen Chen, Qin Zhang,

Songyue Zhang

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(2), P. 584 - 584

Published: Jan. 1, 2024

Language: Английский

Citations

0