Nucleophilic Amination of Aryl Halides with an Azanide Surrogate DOI Creative Commons

Bradley D. Cooper,

Thomas D. Harris,

Ethan R. X. Lim

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 31(8)

Published: Nov. 25, 2024

Abstract We report the development of an azanide ( − NH 2 ) surrogate which enables facile conversion electron‐deficient (hetero)aryl halides into primary N ‐aryl amines under transition‐metal‐free conditions. The designed amidine reagent is easy to prepare, bench stable, and undergoes ‐arylation basic conditions at 40 °C. Intermediate amidines are readily cleaved form in situ through hydrolysis or base‐promoted elimination. developed a safer more selective alternative existing anionic N‐nucleophiles, such as alkali metal amides azide salts.

Language: Английский

Advances in Nickel-Catalyzed O-Arylation of Aliphatic Alcohols and Phenols with (Hetero)aryl Electrophiles DOI
Mark Stradiotto,

Kathleen M. Morrison

Synthesis, Journal Year: 2023, Volume and Issue: 56(02), P. 229 - 238

Published: July 20, 2023

Abstract Transition-metal catalysis has been consequential in enabling carbon–heteroatom bond-forming reactions. Recent breakthroughs Ni-catalyzed cross-couplings have offered competitive and, some cases, superior reactivity to Pd- or Cu-based processes. Amidst the ongoing renaissance this field, C–O cross-coupling of alcohols and (hetero)aryl (pseudo)halides surfaced as an effective strategy for synthesis ethers. Methodologies achieve such transformations tend rely on one three catalytic approaches: (i) thermal conditions often accompanied by ancillary ligand design tailored Ni catalysis; (ii) synergistic combination photoredox (iii) electrochemically driven catalysis. In instances, these protocols provided access expanded substrate scope, including use inexpensive abundant electrophile coupling partners (e.g., chlorides). This Short Review aims summarize recent progress development O-arylations primary, secondary, tertiary aliphatic alcohols, well phenols, with electrophiles. 1 Introduction 2 Thermally Promoted Cross-Coupling 2.1 Primary Secondary Aliphatic Alcohols 2.2 Tertiary 2.3 Phenols 3 Photochemically 3.1 3.2 4 Electrochemically 4.1 5 Conclusions Outlook

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

Organocatalyzed diastereoselective cyclization of β-alkyl nitroolefins with alkylidene malononitriles: new approach to azetidine nitrones and isoxazoles DOI

Shikha Singh Rathor,

Ashvani K. Patel, Sampak Samanta

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(6), P. 1782 - 1789

Published: Jan. 1, 2024

An organocatalytic domino reaction of β-alkyl nitroolefins with alkylidene malononitriles to give azetidine nitrones good diastereoselectivities is reported. The in situ -generated were transmuted into isoxazoles catalyzed by acid.

Language: Английский

Citations

2

Progress in Electrochemically Empowered C−O Bond Formation: Unveiling the Pathway of Efficient Green Synthesis DOI

Debosmit Ghosh,

Aroop Kumar Samal,

Anita Parida

et al.

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: 19(11)

Published: April 8, 2024

Abstract (C−X) bonds (X=C, N, O) are the main backbone for making different skeleton in organic synthetic transformations. Among all sustainable techniques, electro‐organic synthesis C−X bond formation is advanced tool as it offers a greener and more cost‐effective approach to chemical reactions by utilizing electrons reagents. In this review, we want explore recent advancements electrochemical C−O formation. The electrochemically driven represents an emerging exciting area of research. context, techniques numerous advantages, including higher yields, cost‐efficient production, simplified work‐up procedures. This method enables continuous consistent molecules, significantly enhancing overall reaction yields. Furthermore, both intramolecular intermolecular forming provided valuable products O‐containing acyclic/cyclic analogue. Hence, carbonyl (C=O), ether ‐O‐), ester (‐COOR) functionalization cyclic/acyclic analogues have been prepared continuously via innovative pathway. discuss one‐decade pathways various contains functional group chronological manner. review focused on aspects mechanistic path has also mentioned critical finding regarding pathways.

Language: Английский

Citations

2

VSP-2 attenuates secretion of inflammatory cytokines induced by LPS in BV2 cells by mediating the PPARγ/NF-κB signaling pathway DOI Creative Commons

Jingxin Cui,

Liwei Xu,

Yimeng Sun

et al.

Open Life Sciences, Journal Year: 2024, Volume and Issue: 19(1)

Published: Jan. 1, 2024

Neuroinflammation, characterized by microglial activation and the subsequent secretion of inflammatory cytokines, plays a pivotal role in neurodegenerative diseases brain injuries, often leading to neuronal damage death. Alleviating neuroinflammation has thus emerged as promising strategy protect neurons ameliorate disorders. While peroxisome proliferator-activated receptor gamma (PPARγ) agonists have demonstrated potential therapeutic actions on neuroinflammation, their prolonged use, such with rosiglitazone, can lead cardiac risks lipid differentiation In this study, we investigated effects newly synthesized PPARγ agonist, VSP-2, cytokines BV2 cells. Treatment VSP-2 significantly reduced mRNA protein levels proinflammatory interleukin-1β (IL-1β), IL-6, tumor necrosis factor-α (TNF-α). Furthermore, attenuated phosphorylation nuclear factor kappa B (NF-κB) (65 kD) IκBα, well translocation NF-κB kD). Additionally, use small interfering RNA was able attenuate pathway. conclusion, our findings suggest that effectively suppressed expressions IL-1β, TNF-α via PPARγ/NF-κB signaling Given its benefits, may emerge candidate for treatment or injuries associated neuroinflammation.

Language: Английский

Citations

1

Transition‐Metal Free Arylation of Therapeutically Important Heterocycles DOI

Ambarish Priyadarshan,

G. Tripathi, Venneti N. Murty

et al.

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(19)

Published: May 15, 2024

Abstract The transition‐metal‐free synthesis of organic compounds especially heterocycles is in resonance with one the twelve principles proposed by Prof. Paul Anastas his renowned work towards sustainable development green chemistry. Traditional‐metal‐catalyzed reactions often involve expensive or toxic metal catalysts, and there a growing interest developing more environmentally friendly methods. arylation an important area research chemistry, particularly biologically active pharmaceuticals. Arylation at different positions enhances potency stability pharmaceutically scaffolds. In this review, overview synthetic protocols developed for variety heterocyclic including, pyrroles, pyridines, thiophene, indole, oxindoles, purines, xanthene, etc. has been described.

Language: Английский

Citations

1

Transition‐Metal‐Free Chemo‐Selective C‐C/C‐N Bond Formation Reaction for the Highly Efficient Synthesis of Pyrazoles, Pyrazolo fused Pyrimidines and Pyridines DOI
Nikita Goel,

Pradeep Kumar,

Sunita Bhagat

et al.

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

Published: July 19, 2024

Abstract Pyrazoles and pyrazolo fused pyrimidines pyridines are well known for their applications in various fields like pharmaceuticals, agrochemicals materials sciences. Keeping this mind herein, we have developed the transition‐metal‐free approach chemo‐selective synthesis of pyrazole its derivatives from acetopheneones. The selectivity reaction can easily be tuned by shifting acidic to basic medium pyrazolo‐pyrirmidines pyrazolo‐pyridines respectively. shows excellent functional group tolerance form −F, −Cl, −Br, −NMe 2 , −OH, −OMe, −B(OH) good yields.

Language: Английский

Citations

1

Silver‐Catalyzed Synthesis of Benzyl Ethers via Alkoxylation of Benzylic C(sp3)−H Bonds DOI
Peng Huang,

Guangan Zhang,

Zechao Wang

et al.

Chemistry - An Asian Journal, Journal Year: 2023, Volume and Issue: 18(14)

Published: May 31, 2023

Alkoxylation of benzylic C(sp3 )-H bonds has become one the most important tools for construction benzyl ethers from feedstock chemicals. Herein, we reported a silver catalyzed alkoxylation employing potassium persulfate as an oxidant at room temperature. This strategy showed good functional-group tolerance, site selectivity, and chemoselectivity. The reaction proceeded smoothly in presence various primary, secondary, tertiary alcohol nucleophiles, affording corresponding ethers. Combined experimental studies provided mechanistic insights into possible radical pathways. Furthermore, mechanism was proposed this method.

Language: Английский

Citations

3

Nickel-Catalyzed O-Arylation of Primary or Secondary Aliphatic Alcohols with (Hetero)aryl Chlorides: A Comparison of Ni(I) and Ni(II) Precatalysts DOI

Kathleen M. Morrison,

Nicholas J. Roberts, Samantha L. Dudra

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 89(22), P. 16126 - 16133

Published: Dec. 13, 2023

A comparative experimental and computational study examining the interplay of ancillary ligand structure Ni oxidation state in Ni-catalyzed C(sp

Language: Английский

Citations

2

Boric Acid-Grafted Biochar (BoAB) for the Direct Amidation of Carboxylic Acids and Amines DOI
Adhish Singh, Mohit Kapoor

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(19), P. 8589 - 8596

Published: Jan. 1, 2024

Boric acid grafted biochar was developed and explored for its potential in the amidation of unactivated carboxylic acids amines under mild conditions.

Language: Английский

Citations

0