An Unexpected Synthesis of 2-Sulfonylquinolines via Deoxygenative C2-Sulfonylation of Quinoline N-Oxides with Sulfonyl Chlorides DOI Creative Commons
Wei Yang,

Zhong-Ying Tian,

Ying-Jun Lin

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(12), P. 2863 - 2863

Published: June 16, 2024

A mild, efficient and practical protocol for the preparation of 2-sulfonylquinolines through CS2/Et2NH-induced deoxygenative C2-H sulfonylation quinoline N-oxides with readily available RSO2Cl was developed. The reaction proceeded well under transition-metal-free conditions exhibited a wide substrate scope functional group tolerance. preliminary studies suggested that nucleophilic sulfonyl sources were generated in situ via CS2, Et2NH chlorides.

Language: Английский

Synthesis of S-alkyl phosphorothioates/phosphorodithioates via ring-opening reaction of sulfonium salts with S8, H-phosphonates or P4S10, and alcohols DOI
Lihua Yang, Lin Chen,

Bei Li

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(20), P. 5731 - 5740

Published: Jan. 1, 2024

A simple and practical method for the synthesis of S -alkyl phosphorothioates/phosphorodithioates through three-component reaction cyclic sulfonium salts with 8 , H -phosphonates, or P 4 10 alcohols was readily developed.

Language: Английский

Citations

4
Trinuclear Borane (B3H7)-Mediated Selective C4–H Alkylation and Phosphonation of Quinolines and Tetrahydroquinolines DOI

Qiao‐Jing Pan,

Sihan Jia,

Zi‐Heng Fan

et al.

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

Published: Jan. 1, 2025

Herein, we report a method for the regioselective alkylation and phosphonation of quinoline C4–H via B3H7-mediated nucleophilic addition Turbo Grignard reagents phosphine oxide anions to quinolines bearing different substituents, affording 4-alkyl 4-phosphoryl tetrahydroquinolines after one-pot oxidation or reduction. The results indicate that coordination B3H7 group can activate substrates toward potential 1,4-dearomative subtly control regioselectivity by preventing 1,2-dearomative addition.

Language: Английский

Citations

0
Visible-Light-Induced Phosphorothioation of Alkenyl Sulfonium Salts with S8 and H-Phosphonates DOI
Lihua Yang,

Ni-Dan Meng,

Li Tang

et al.

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

Published: Feb. 4, 2025

An efficient and practical method for synthesizing vinyl phosphorothioates has been demonstrated through a visible-light-induced three-component reaction of alkenyl sulfonium salts, S8, H-phosphonates. This facilitates the synthesis diverse range with wide substrate scope functional group tolerance. Preliminary mechanistic studies suggest that involves phosphorothioate radical-triggered process.

Language: Английский

Citations

0
Synthesis of S-Alkyl Dithiocarbamates via Multicomponent Reaction of Cyclic Sulfonium Salts with CS2 and Amines DOI

Li Yang,

Jia Shu, Yun Liu

et al.

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

Published: Oct. 3, 2024

A convenient and practical method for the synthesis of various

Language: Английский

Citations

3
Recent Advances on Direct Phosphorothiolation Reactions DOI

Haifa Zheng,

Ju Peng,

Xiang Liu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: July 23, 2024

Abstract Organophosphorothioates are organic molecules containing sulfur and phosphorus, with significant biological activity physicochemical properties, widely used in synthesis, medicinal chemistry, the agrochemical industry. In particular, many phosphorothioates display a variety of activities, such as antifungal, antibacterial, anti‐parasite, anticancer, so on. Traditionally, synthesis has mainly relied on indirect methods involving construction S−P bond. recent years, direct phosphorothiolation gained attention reliable rapid method for introducing −S−P(O)(OR) 2 group into parent molecules. This article reviews latest advances reactions, categorized based different sources group.

Language: Английский

Citations

2
New Frontiers in Phosphorothioate Formation: Harnessing Inorganic Phosphorus Sources DOI
Jiawei He,

Xuesi Zhou,

Zixuan Wan

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(99), P. 14691 - 14702

Published: Jan. 1, 2024

This review highlights the latest advancements in synthesis of phosphorothioates and their derivatives from inorganic phosphorus sources, focusing on applicability, mechanisms, current limitations, potential future directions.

Language: Английский

Citations

0
An Unexpected Synthesis of 2-Sulfonylquinolines via Deoxygenative C2-Sulfonylation of Quinoline N-Oxides with Sulfonyl Chlorides DOI Creative Commons
Wei Yang,

Zhong-Ying Tian,

Ying-Jun Lin

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(12), P. 2863 - 2863

Published: June 16, 2024

A mild, efficient and practical protocol for the preparation of 2-sulfonylquinolines through CS2/Et2NH-induced deoxygenative C2-H sulfonylation quinoline N-oxides with readily available RSO2Cl was developed. The reaction proceeded well under transition-metal-free conditions exhibited a wide substrate scope functional group tolerance. preliminary studies suggested that nucleophilic sulfonyl sources were generated in situ via CS2, Et2NH chlorides.

Language: Английский

Citations

0