Photocatalytic difunctionalization of alkenes with quinoxalinones and dialkyl dithiophosphoric acids DOI

Zhen Wang

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

The photoredox eosin Y-catalyzed difunctionalization of alkenes with quinoxalinones and dialkyl dithiophosphoric acids was realized. This reaction exhibited excellent functional group compatibility.

Language: Английский

Paired Electrolysis-Enabled Arylation of Quinoxalin-2(1H)-ones DOI

Jia-Cheng Hou,

Jun Jiang,

Yan-Cui Wen

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(9), P. 6117 - 6125

Published: April 24, 2024

The first paired electrolysis-enabled arylation of quinoxalin-2(1H)-ones was achieved using cyanoarenes as the reagents. A variety 3-arylquinoxalin-2(1H)-ones with various important functional groups were obtained in moderate to good yields under metal- and chemical oxidant-free conditions. With a pair reductive oxidative processes occurring among substrates reaction intermediates, power consumption can be dramatically reduced.

Language: Английский

Citations

22

Multicomponent Heteroarylphosphorothiolation of Alkenes for Accessing β‐Phosphorothiolated Quinoxalinones DOI
Sha Peng, Lihua Yang,

Xiang-Qin Xu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(12), P. 2758 - 2763

Published: April 24, 2024

Abstract Herein, we present a (NH 4 ) 2 S O 8 mediated difunctionalization reaction of aryl alkenes with quinoxalinones and P(O)SH compounds. This method enables the synthesis various phosphorothioate‐containing quinoxalin‐2(1 H )‐one derivatives (46 examples) in 37–79% yields. The is compatible range functional groups easily adaptable to large‐scale synthesis. Preliminary studies suggest involvement phosphorothioate radicals these transformations.

Language: Английский

Citations

10

Visible-Light Photoredox-Catalyzed Difunctionalization of Alkynes with Quinoxalin-2(1H)-Ones, P4S10, and Alcohols DOI

Lianhui Song,

Chao Ma,

Jian Huang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10974 - 10986

Published: July 24, 2024

Visible-light photoredox-catalyzed method has been developed for the synthesis of quinoxalin-2(1H)-one-containing vinyl phosphorodithioates via direct difunctionalization alkynes with quinoxalin-2(1H)-ones, P4S10 and alcohols. This four-component reaction could be carried out under metal-free mild conditions, affording a number in moderate to good yields Z-isomers as major products. Photocatalytic radical mechanism is proposed based on results trapping fluorescence quenching experiments.

Language: Английский

Citations

4

K2S2O8‐Mediated Access to Alkylsulfonated Spiro[4,5] Trienones from N‐Arylpropiolamides with the Insertion of Sulfur Dioxide DOI

Xin‐Qian Liu,

Peng‐Fei Huang, Biquan Xiong

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 366(3), P. 488 - 493

Published: Dec. 23, 2023

Abstract A four‐component reaction of N ‐arylpropiolamides, Hantzsch esters, Na 2 S O 5 and water via a radical cascade cyclization process with the insertion sulfur dioxide mediated by K 8 is reported. series alkylsulfonated spiro[4,5] trienones are prepared up to 86% yield good functional group tolerance substrate applicability. Preliminary mechanism experiments indicate that carbonyl oxygen originated from water.

Language: Английский

Citations

5

Efficient synthesis of SCF3-containing 3-alkenylquinoxalinones via three-component radical cascade reaction DOI
Siyu Wang,

Chu L,

Wei Yang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(18), P. 3740 - 3745

Published: Jan. 1, 2024

An efficient and practical method for the synthesis of 3-alkenylquinoxalinones containing SCF

Language: Английский

Citations

1

Electrochemical Trifluoromethylthiolation/Cyclization of N-Arylacrylamides with AgSCF3: Access to SCF3-Containing Oxindoles DOI
Yu Wang, Ye Wang, Sheng Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 11950 - 11958

Published: Aug. 19, 2024

An environmentally friendly electrochemical strategy for the synthesis of SCF3-containing oxindoles was developed. This transformation accomplished through a cascade trifluoromethylthiolation/cyclization N-acrylamides with AgSCF3, obviating requirement external oxidants. A variety functional groups were well tolerated in this transformation.

Language: Английский

Citations

1

Photocatalytic difunctionalization of alkenes with quinoxalinones and dialkyl dithiophosphoric acids DOI

Zhen Wang

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

The photoredox eosin Y-catalyzed difunctionalization of alkenes with quinoxalinones and dialkyl dithiophosphoric acids was realized. This reaction exhibited excellent functional group compatibility.

Language: Английский

Citations

0