Intramolecular C–H arylation of pyridine derivatives with a palladium catalyst for the synthesis of multiply fused heteroaromatic compounds DOI Creative Commons

Yuki Nakanishi,

Syuichi Sugita,

Kentaro Okano

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 3256 - 3262

Published: Dec. 13, 2024

The C–H arylation of 2-quinolinecarboxyamide bearing a C–Br bond at the N -aryl moiety is carried out with palladium catalyst. reaction proceeds on pyridine ring adjacent to amide group in presence 10 mol % Pd(OAc) 2 110 °C afford cyclized product 42% yield. yield improved 94% when performed PPh 3 as ligand palladium. examined amides derived from unsubstituted picoline, 6-methylpicoline, and 2,6-pyridinedicarboxylic acid similar manner products 70%, 77%, 87% yield, respectively. related also non-pyridine derivatives terephthal- benzamides multiply fused heterocyclic compounds 81% 89% yields,

Language: Английский

Unveiling a carbazole-based photocatalyst for visible-light-driven synthesis of indolyl diarylmethanes and 2-benzimidazoles DOI
Sunil Kumar, K. R. Justin Thomas

Catalysis Science & Technology, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A carbazole-based photocatalyst (MD) incorporating a dicyanovinyl acceptor and exhibiting superior redox potential has been demonstrated for sustainable photocatalytic approach to synthesize indolyl diarylmethanes 2-substituted benzimidazoles.

Language: Английский

Citations

0
Manganese-Promoted Electrochemical Imino-Pinacol Coupling to Access Vicinal Diamines DOI

Weihao Cui,

Xiaolong Xu, Cong Zhang

et al.

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

Published: March 5, 2025

We herein introduce an electrochemical imino-pinacol coupling reaction to access the vicinal diamine scaffold. This green and convenient protocol employs in situ-generated imines as starting materials deliver a broad range of products under electroreductive conditions. Moreover, this is also applicable pinacol coupling. Mechanistic investigation suggests that Mn(III) additive essential for promoting SET reduction imine material preventing formation over-reduced amine side product.

Language: Английский

Citations

0
Visible‐Light‐Induced C−H Amidation of (Hetero)arenes with Hypervalent Iodine(III) Reagents DOI Open Access
Xiaojuan Wang, He Wang, Zhenkun Ma

et al.

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

Published: March 10, 2025

Abstract A visible‐light‐promoted C−H amidation of (hetero)arenes with hypervalent iodine reagents has been successfully achieved good yields. The high efficiency, broad substrate range and functional group compatibility demonstrated the utility method. Moreover, this protocol was suitable for late‐stage functionalization natural products. Mechanistic studies have shown that N‐centred saccharin radical mediates arenes.

Language: Английский

Citations

0
Designing Peptide-Based Nucleophilic Catalysts Possessing Multiple Identical Active Sites for Late-Stage Chlorination of Peptides and Drugs DOI

Subimal Patra,

Haripriyo Mondal,

Uttam Dash

et al.

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

Published: April 3, 2025

In the quest for developing catalysts with multiple active sites, we designed a series of methionine-based peptide prepared by classical coupling. Given widespread presence aromatic chloro-substituents and their significant pharmacokinetic properties, performance these were evaluated late-stage chlorination tyrosine residue on peptides up to octamer as well drug molecules. The operationally simple reaction conditions, excellent catalyst loading 0.25 mol %, gram-scale reactions are major highlights this method.

Language: Английский

Citations

0
Pyrene-Based Organic Photoredox Catalysts for Carbon–Carbon Bond-Forming Reactions: Reductive Coupling of Aromatic Carbonyl and Imine Compounds DOI
Shusuke Okamoto, Daisuke Nagai

Organic Letters, Journal Year: 2024, Volume and Issue: 26(36), P. 7718 - 7722

Published: Sept. 5, 2024

Metal-free photoredox catalysts built upon a pyrene core were developed for carbon-carbon bond-forming reactions. Among these catalysts, derivative containing urea moiety effectively facilitated the reductive coupling of aromatic carbonyl and imine compounds under blue LED irradiation. This process provided corresponding vicinal diols diamines in good yields.

Language: Английский

Citations

0
Dehydrogenative Photocyclization of 3-Styryl Indoles to Fused Indole Systems DOI Creative Commons
Yunus Taskesenligil, Nurullah Saraçoğlu

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

Published: Nov. 7, 2024

The synthesis of 5-aryl- or 5,6-diaryl-11

Language: Английский

Citations

0
Intramolecular C–H arylation of pyridine derivatives with a palladium catalyst for the synthesis of multiply fused heteroaromatic compounds DOI Creative Commons

Yuki Nakanishi,

Syuichi Sugita,

Kentaro Okano

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 3256 - 3262

Published: Dec. 13, 2024

The C–H arylation of 2-quinolinecarboxyamide bearing a C–Br bond at the N -aryl moiety is carried out with palladium catalyst. reaction proceeds on pyridine ring adjacent to amide group in presence 10 mol % Pd(OAc) 2 110 °C afford cyclized product 42% yield. yield improved 94% when performed PPh 3 as ligand palladium. examined amides derived from unsubstituted picoline, 6-methylpicoline, and 2,6-pyridinedicarboxylic acid similar manner products 70%, 77%, 87% yield, respectively. related also non-pyridine derivatives terephthal- benzamides multiply fused heterocyclic compounds 81% 89% yields,

Language: Английский

Citations

0