Visible‐Light‐Mediated Synthesis of α‐Ketoamides via Oxidative Amination of 2‐Bromoacetophenones Using Eosin Y as a Photoredox Catalyst DOI

Kaushal Kishor,

Neha Sharma Prabhakar,

Krishna Nand Singh

et al.

Chemistry - An Asian Journal, Journal Year: 2023, Volume and Issue: 18(19)

Published: Aug. 29, 2023

An oxidative amination of 2-bromoacetophenones has been accomplished to provide α-ketoamides by using photoredox catalysis with air as oxidant. The reactants are readily accessible, and the method is endowed broad substrate scope good functional group tolerance. practicality approach also shown a gram-scale reaction.

Language: Английский

Divergent Synthesis of Tetrasubstituted Phenols via [3 + 3] Cycloaddition Reaction of Vinyl Sulfoxonnium Ylides with Cyclopropenones DOI
Shaoyong Chen, Yao‐Fu Zeng,

Wen‐Xuan Zou

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(23), P. 4286 - 4291

Published: June 2, 2023

Two categories of tetrasubstituted phenols were prepared via the cycloaddition reaction vinyl sulfoxonnium ylides with cyclopropenones in a switchable manner. Copper carbenoid was proposed as active intermediate process 2,3,4,5-tetrasubstituted formation, while 2,3,5,6-tetrasubstituted generated direct [3 + 3] annulation under metal-free conditions. Further synthetic applications also demonstrated.

Language: Английский

Citations

22
Synthesis of α-Carbonyl-α′-amide Sulfoxonium Ylides from Isocyanates with Complete Atom Economy DOI

Ajay Kant Gola,

Ajay Sharma, Satyendra Kumar Pandey

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(7), P. 1214 - 1217

Published: Feb. 9, 2023

An efficient catalyst- and additive-free facile synthesis of α-carbonyl-α′-amide sulfoxonium ylides from isocyanates β-ketosulfoxonium with complete atom economy has been described. The adorned various functional groups were well-tolerated afforded moderate to high yields the ylide derivatives. Finally, using large-scale reactions converting synthesized into other valuable compounds, we demonstrated practicality this synthetic method.

Language: Английский

Citations

18
A Platform for the Synthesis of Diverse Phosphonyl and Thiofunctionalized Sulfoxonium Ylides DOI

Wen‐Xuan Zou,

Qiong Hu,

Dan‐Ting Shen

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(27), P. 5811 - 5816

Published: June 28, 2024

A practical strategy for the construction of diverse phosphonyl and thiofunctionalized sulfoxonium ylides via controllable monofunctionalization hybrid I(III)/S(VI) is presented. This process allows efficient P–H insertion under Cu catalysis, enabling synthesis ylides, whereas reaction with sulfur-containing reagents including AgSCF3, KSC(S)OR, KSCN mild conditions resulted in α-trifluoromethylthiolation, dithiocarbanation, thiocyanation accordingly. Of note, wide substrate compatibility (108 examples), excellent efficiency (up to 99% yield), gram-scale experiments, various product derivatizations highlight synthetic utility this protocol.

Language: Английский

Citations

7
Synthesis of α-ketothioamides with elemental sulfur under solvent-free conditions in a mixer mill DOI Creative Commons
Chandan Chittapriya Sahu, Sourav Biswas, Renè Hommelsheim

et al.

RSC Mechanochemistry, Journal Year: 2024, Volume and Issue: 1(1), P. 38 - 42

Published: Jan. 1, 2024

α-Ketothioamides are formed by a mechanochemical solvent-free Willgeroth–Kindler-type reaction starting from acetophenone derivatives, amines, and elemental sulfur.

Language: Английский

Citations

6
Elemental Sulfur-Mediated Synthesis of Quinoxalines from Sulfoxonium Ylides DOI

Trayambek Nath Chaubey,

Paran J. Borpatra, Satyendra Kumar Pandey

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(28), P. 5329 - 5332

Published: July 7, 2023

A novel straightforward and catalyst-free approach for synthesizing quinoxaline derivatives from sulfoxonium ylides o-phenylenediamines mediated by elemental sulfur has been described. Due to the simple mild reaction conditions, decorated with different functional groups furnished moderate high yields of were well tolerated. Finally, large-scale reactions, synthesis pyrazines, some bioactive compounds are used illustrate potential utility developed approach.

Language: Английский

Citations

14
Towards More Practical Methods for the Chemical Synthesis of Thioamides Using Sulfuration Agents: A Decade Update DOI Creative Commons
Qiang Zhang, Laurent Soulère, Yves Queneau

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(8), P. 3527 - 3527

Published: April 17, 2023

Compounds possessing a thioamide function play crucial role in organic synthesis, serving as key building blocks. They are also important the pharmaceutical chemistry and drug design, owing to their ability mimic amide biomolecules while retaining or developing biological activity. From synthetic viewpoint, several methods have been developed for preparing thioamides using sulfuration agents. The purpose of this review is give an update last decade contributions focusing on formation employing different sulfur sources. When appropriate, cleanness practicality new highlighted.

Language: Английский

Citations

12
tert‐Butyl Hydroperoxide (TBHP): Recent Progress in C−H Functionalization and Heteroatom‐Heteroatom Bond Formations DOI Open Access
Ravi Varala,

Vittal Seema,

Mohamed Hussein

et al.

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(30)

Published: Aug. 6, 2024

Abstract tert‐ Butyl hydroperoxide (tBuOOH, TBHP) is a commonly used in many oxidation processes. The primary factors contributing to the increasing usefulness of TBHP include its affordability, eco‐friendliness, exceptional efficacy, and capacity substitute harmful or rare heavy metal oxidants. In this sexennial update, we thoroughly critically examined most noteworthy applications C−H functionalization heteroatom‐heteroatom bond formation reactions from 2018 till present. review has been subdivided based on nature bonds being formed. focuses advantages disadvantages using synthetic organic transformations, as well breadth their use underlying mechanisms involved.

Language: Английский

Citations

4
Selective Synthesis of Bromo‐substituted 2H‐Pyrroles and 3H‐Pyrroles via Three‐Component Cascade Annulation of 1,3‐Enynes, NBS and TMSN3 DOI Open Access
Zhen Zhang,

Qingting Song,

Fan Qin

et al.

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 19, 2025

Comprehensive Summary A novel and efficient method for selective synthesis of bromo‐substituted 2 H ‐pyrroles 3 has been achieved from 1,3‐enynes, NBS TMSN via O‐promoted cyclization reactions or TFA‐catalyzed cyclization/2,3‐shift reactions, providing a range structurally diverse products in moderate to good yields under mild conditions.

Language: Английский

Citations

0
Programmable Strategies for the Conversion of Aldehydes to Unsymmetrical (Deuterated) Diarylmethanes and Diarylketones DOI Creative Commons
Vipin R. Gavit, Nicole Hanania, Nadim Eghbarieh

et al.

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

Published: March 28, 2025

Herein, we present a versatile method for synthesizing unsymmetrical diarylmethanes and diarylketones from aldehydes arenes. This involves: (1) regioselective Ar-H alkylation to form benzhydrylphosphonium salts via one-pot, four-component reaction with simple reagents (2) chemoselective reductions or oxidations of the benzylic C-P bond. Notably, D2O yield fully deuterated diarylmethanes. high-yielding, straightforward approach offers valuable building blocks enables novel transformations academic pharmaceutical research.

Language: Английский

Citations

0
Photocatalytic synthesis of dual acylmethylation derivates of indole[2,1-a]isoquinolinones via tandem cyclization/C3 acyl methylation DOI
Zongbo Xie, Wenli Li, Weiwei Zhang

et al.

Molecular Catalysis, Journal Year: 2025, Volume and Issue: 580, P. 115058 - 115058

Published: April 15, 2025

Language: Английский

Citations

0