Cu‐Catalyzed Coupling of Sulfonyl Chlorides with Alkenes: Synthesis of Dienyl Sulfones and β‐Chlorosulfones DOI Open Access
Priyanka Choudhary,

Ravikant S. Ranjan,

Rodney A. Fernandes

et al.

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

Published: Oct. 14, 2024

Abstract This work reports a Cu‐catalyzed coupling technique for synthesizing ( E )‐dienyl sulfones and β‐chlorosulfones from 1‐arylbutadienes styrenes, respectively. By employing easily available inexpensive reagents, this method enables the synthesis of diverse array dienyl with excellent functional group tolerance under base‐ oxidant‐free conditions. It also proves versatile late‐stage functionalization drug molecules scale‐up reactions. The showcases notable selectivity, gentle reaction conditions, compatibility various groups as demonstrated through 66 examples display regioselectivity.

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
Copper-catalyzed sulfonylation of alkenes with CH3SSO3Na DOI Creative Commons
Xiaoli Chen, Ge Wu

BMC Chemistry, Journal Year: 2025, Volume and Issue: 19(1)

Published: Feb. 22, 2025

A successful methodology for the copper-catalyzed dehydrogenated methylsulfonylation of alkenes utilizing CH3SSO3Na in conjunction with hypervalent iodine reagents was successfully established. This method offers a practical avenue to obtain allyl methyl sulfones and alkenyl by forming C-S bonds. Using C-H bond oxidation sulfonylation strategy Bunte salts, we synthesized total twenty two compounds, including four examples deuterium-substituted molecules, demonstrated one example scale-up reaction.

Language: Английский

Citations

0
Radical-mediated sulfonylation relay of alkyl alkynes/alkenes and electron-deficient alkenes to access vinyl and alkyl sulfones DOI
Jinhui Liu,

Fang Long,

Qing Li

et al.

Organic Chemistry Frontiers, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A radical-mediated sulfonylation relay of alkyl alkynes/alkenes with electron-deficient alkenes using Na 2 S O 4 as a linker is developed to synthesize highly selective ( Z )-vinyl and sulfones under metal-free catalyzed system.

Language: Английский

Citations

0
Manual Grinding and Sunlight Synergistically Promoted Sulfonylation of Alkenyl Sulfonium Salts with Sulfinic Acids DOI
Lihua Yang, Lin Chen, Weijun Yao

et al.

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

Published: April 10, 2025

An environmentally friendly and practical method for the synthesis of various vinyl sulfones was developed through direct sulfonylation alkenyl sulfonium salts with sulfinic acids. The reaction effectively triggered by combined actions milling, sunlight, photocatalysts under solvent-free conditions, offering advantages such as a short time (5-10 min), room temperature, straightforward workup procedure. Preliminary mechanistic studies suggested that sulfonyl radical may be involved in this mechanophotocatalytic transformation process.

Language: Английский

Citations

0
Visible-Light-Mediated Addition Reactions of Sulfur-Containing Reagents with α-Trifluoromethyl Alkenes DOI
Yi‐Rong Chen, Jiahui Han, Weidong Rao

et al.

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

Published: April 22, 2025

Herein, we described the addition reactions of sulfur-containing reagents (sodium sulfinates, dithiosulfonates) with α-trifluoromethyl alkenes under visible light. A series trifluoromethyl sulfonates were synthesized via visible-light-induced radical reaction sodium sulfinates and to obtain protons from solvent. dithiosulfonated derivatives bifunctionalization dithiosulfonates.This strategy has advantages mild conditions, good substrate universality high yield up 99% yield.

Language: Английский

Citations

0
The crystal structure of catena-((μ 2-4,4′-bipyridine-κ 2 N:N′)-bis(4-fluorobenzoato-κ1O)-copper(II)), C24H16F2N2O4Cu DOI Creative Commons
Wentao Chen,

J. J. Qin,

Hangyi An

et al.

Zeitschrift für Kristallographie - New Crystal Structures, Journal Year: 2025, Volume and Issue: unknown

Published: April 28, 2025

Abstract C 24 H 16 F 2 N O 4 Cu, triclinic, P 1 ‾ $P\overline{1}$ (no. 2), a = 5.3203(6) Å, b 9.0861(11) c 11.5282(10) α 103.718(9)°, β 97.964(9)°, γ 98.771(10)°, V 526.12(10) Å 3 , Z 1, R gt ( ) 0.0497, wR ref 0.1000, T 298 K.

Citations

0
Halogen-bond-promoted direct cross-coupling of ethyl 3-bromo-3-alkyl-2,2-difluoropropanoates with coumarins/quinolinones DOI
Guoliang Pu,

Shi-Yuan Song,

Yang Jian

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(12), P. 3320 - 3325

Published: Jan. 1, 2024

A practical method for the cross-coupling of ethyl 3-bromo-3-alkyl-2,2-difluoropropanoates with coumarins/quinolinones was developed. The IC 50 values 3l against Huh-7 and A549 cells were determined to be 4.6 μM 6.8 μM, respectively.

Language: Английский

Citations

3
EDA Complex-Promoted Cascade Cyclization of Alkynes Enabling the Rapid Assembly of 3-Sulfonylindoles and Vinyl Sulfone Oxindoles DOI
Min Li,

Qiujian Tan,

Xiang Lyu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(27), P. 5799 - 5804

Published: July 2, 2024

Herein, we disclose a photoinduced radical cascade cyclization of alkynes with sulfinates via novel EDA complex for the synthesis various 3-sulfonylindoles and vinyl sulfone oxindoles, which are crucial motifs in medicinal biological chemistry. The reaction proceeds under mild, photocatalyst- transition-metal-free conditions, featuring operational simplicity, broad substrate scope, easy scalability. Mechanistic studies reveal that is initiated intermolecular charge transfer from to N-sulfonamides, generating sulfonyl followed by an N-centered radical, thus enabling process.

Language: Английский

Citations

1
Visible-Light-Induced Synthesis of Vinyl Sulfones via Decarboxylative Sulfonylation of Cinnamic Acids Using Sulfonylazides/p-Toluenesulfonylmethyl Isocyanide/β-Keto Sulfones DOI

Km Ishu,

Mahesh Kumar,

Krishna Nand Singh

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10919 - 10928

Published: July 16, 2024

An efficient visible-light-induced synthesis of vinyl sulfones has been accomplished via decarboxylative sulfonylation cinnamic acids using sulfonylazides,

Language: Английский

Citations

1
Visible-Light-Driven Synthesis of Alkenyl Thiocyanates: Novel Building Blocks for Diverse Sulfur-Containing Molecular Assembly DOI Creative Commons
Helena F. Piedra, Manuel Plaza

Chemical Science, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

A new photochemical method to prepare alkenyl thioethers under both batch and continuous flow conditions is presented. These versatile building blocks enable the synthesis of various organosulfur compounds, highlighting utility this procedure.

Language: Английский

Citations

1