Facile Cleavage of Activated Ketones: An Access to Thioethers via In Situ Generation of Anhydrides by Pummerer-Type Rearrangement DOI
C Sivaraj, Karthick Muthuvel,

Ajay Thonipalliyalil Udayan

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(10), P. 7020 - 7026

Published: April 25, 2024

Herein, we report an oxygen insertion in activated ketones from simple inorganic carbonates for the synthesis of symmetric aromatic anhydrides. For first time, Li2CO3 acts as source and situ generated anhydrides undergo Pummerer-type rearrangement to access α-benzoyloxy–thioethers. Attractively, this protocol occurs under metal-, ligand-, oxidant-free conditions is compatible with a wide range substrates. Control experiments reveal reaction pathway.

Language: Английский

Palladium-Catalyzed Decarbonylative Nucleophilic Halogenation of Acid Anhydrides DOI Open Access
Tian Tian,

Shuhei Uei,

Weidan Yan

et al.

Catalysts, Journal Year: 2025, Volume and Issue: 15(2), P. 191 - 191

Published: Feb. 19, 2025

In this study, we developed a palladium-catalyzed decarbonylative nucleophilic halogenation reaction using inexpensive and readily available acid anhydrides as substrates. This approach effectively circumvents the instability of acyl chlorides low reactivity fluorides. The Pd/Xantphos catalyst system exhibited excellent compatibility with thermodynamically kinetically challenging reductive elimination C–X bonds (X = I, Br, Cl) from Pd(II) intermediates. Notably, for electron-donating substrates, adopting an open significantly improved efficiency. positive effect may be due to reversible nature CO insertion deinsertion, which helps direct toward desired pathway by allowing generated exit system. Mechanistic studies suggest that proceeds through highly reactive halide intermediate, followed unimolecular fragment coupling (UFC) via decarbonylation or alternative involving formation activated anionic palladate complex in presence lithium halide.

Language: Английский

Citations

0
Reductive cross-coupling of N-acyl pyrazole and nitroarene using tetrahydroxydiboron: synthesis of secondary amides DOI

Hayeon Moon,

Sunwoo Lee

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(41), P. 8329 - 8334

Published: Jan. 1, 2023

We report on a new method for the synthesis of amides using acyl pyrazoles and nitroarenes under reducing conditions. It was found that react with organo-nitro compounds in presence B2(OH)4, giving corresponding good yields. demonstrated benzoyl having various substituents different can be used to produce range N-substituted benzamides. The shows functional group tolerance has potential application variety organic molecules.

Language: Английский

Citations

6
Solid-state synthesis of lead-free perovskite Cs3Bi2Br9 for photocatalytic O2-involved coupling of aldehydes or alcohols to anhydrides DOI
Qiangwen Fan,

Dawei Liu,

Yuan Hu

et al.

Journal of Catalysis, Journal Year: 2024, Volume and Issue: unknown, P. 115750 - 115750

Published: Sept. 1, 2024

Language: Английский

Citations

1
Batch vs Continuous‐Flow Method to Synthesize N‐(3‐acylamidopropyl)lactams through N‐C Bond Cleavage in Amides with Amidines DOI
Karthick Govindan, Nian‐Qi Chen,

Gokulakannan Venkatachalam

et al.

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

Published: Nov. 2, 2024

Abstract The selective N−C bond cleavage of amides to create value‐added products through a transition metal‐free approach has become significant challenge. Here, we present method convert into N ‐(3‐acylamidopropyl)lactams sequential amide chemoselective and amidine ring opening under mild conditions, applicable in batch continuous flow processes. These methods utilize bench‐stable reagents are operationally straightforward mild, enabling synthesis on gram scale with excellent functional group tolerance. Additionally, the synthetic feasibility these reactions conditions proven be highly efficient, providing ‐(3‐acylamidopropyl)lactam derivatives improved yields shorter reaction time.

Language: Английский

Citations

1
Nickel‐Catalyzed Isotopic Labeling: Synthesis of Oxygen‐18‐Labeled Esters from Amides DOI

Nithin Pootheri,

Sunwoo Lee

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(22), P. 3950 - 3957

Published: Oct. 7, 2023

Abstract A method is developed for preparing 18 O‐labeled esters through a Ni‐catalyzed three‐component reaction of amides, alkyl halides, and water. This demonstrated excellent selectivity compatibility with various amides allowing the synthesis diverse isotopically labelled esters. bromides, carboxylates that generated from water in presence base formed desired

Language: Английский

Citations

2
Facile Cleavage of Activated Ketones: An Access to Thioethers via In Situ Generation of Anhydrides by Pummerer-Type Rearrangement DOI
C Sivaraj, Karthick Muthuvel,

Ajay Thonipalliyalil Udayan

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(10), P. 7020 - 7026

Published: April 25, 2024

Herein, we report an oxygen insertion in activated ketones from simple inorganic carbonates for the synthesis of symmetric aromatic anhydrides. For first time, Li2CO3 acts as source and situ generated anhydrides undergo Pummerer-type rearrangement to access α-benzoyloxy–thioethers. Attractively, this protocol occurs under metal-, ligand-, oxidant-free conditions is compatible with a wide range substrates. Control experiments reveal reaction pathway.

Language: Английский

Citations

0