A selective N-arylation of cyclic amides and amines in DMF and water, respectively, catalysed by Cu(II) /Al2 O3 has been achieved. This protocol has been employed for the synthesis of a library of arenes bearing a cyclic amide and an amine moiety at two ends, including a few scaffolds of therapeutic importance. The mechanism has been established based on detailed electron paramagnetic resonance (EPR) spectroscopy, X-ray photoelectron spectroscopy (XPS), UV diffuse reflectance spectroscopy (DRS) and inductively coupled plasma-mass spectrometry (ICP-MS) studies of the catalyst at different stages of the reaction. The Cu(II) /Al2 O3 catalyst was recovered and recycled for subsequent reactions.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/chem.201302645 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Ligand-Controlled C2- or C3-Selectivity Switching in the Palladium-Catalyzed C-H Arylation of Nonsubstituted 1-Pyrrole.
Org Lett
January 2025
School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.
The C2- or C3-selective direct C-H arylation of nonsubstituted 1-pyrrole with aryl chlorides/nonaflates was achieved using catalysts derived from palladium and appropriate phosphine ligands. The site selectivity of the arylation can be switched by changing the ligands, and the C3-selective arylation of nonsubstituted 1-pyrrole was realized for the first time. BuOLi played an important role in suppressing N-arylation and accelerating C2- or C3-arylation.
View Article and Find Full Text PDFFluorescence-Based Simple and Practical Assay Method for DNA Damage Analysis in DNA-Encoded Library Synthesis.
Bioconjug Chem
December 2024
Department of Chemistry, Gwangju Institute of Science and Technology (GIST), Gwangju 61005, Republic of Korea.
The dsDNA-selective fluorescent-dye-based DNA damage assay was developed for DNA-encoded library (DEL) synthesis. For the various DEL synthesis conditions, the assay was validated through cross-checking with high-performance liquid chromatography (HPLC) analysis, and the fact was confirmed that the usage of a specific ratio of organic solvent can critically induce DNA damage. Also, the applicability of the assay was confirmed through the screening of the DNA-damaging condition of the on-DNA amide coupling reaction and Pd-catalyzed on-DNA -arylation reaction.
View Article and Find Full Text PDFNucleophilic Amination of Aryl Halides with an Azanide Surrogate.
Chemistry
November 2024
Department of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL, UK.
We report the development of an azanide (NH) surrogate which enables the facile conversion of 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 facile N-arylation under basic conditions at 40 °C. Intermediate N-aryl amidines are readily cleaved to form N-aryl amines in situ through hydrolysis or base-promoted elimination.
View Article and Find Full Text PDFMapping Electrophile Chemoselectivity in DalPhos/Nickel N-Arylation Catalysis: The Unusual Influence of Remote Sterics.
Chemistry
November 2024
Department of Chemistry, Dalhousie University, 6274 Coburg Road, P.O. Box 15000, Halifax, Nova Scotia, B3H 4R2, Canada.
We disclose herein our evaluation of competitive (hetero)aryl-X (X: Br>Cl>OTf) reactivity preferences in bisphosphine/Ni-catalyzed C-N cross-coupling catalysis, using furfurylamine as a prototypical nucleophile, and employing DalPhos and DPPF as representative ancillary ligands with established efficacy. Beyond this general (pseudo)halide ranking, other intriguing structure-reactivity trends were noted experimentally, including the unexpected observation that bulky alkyl (e. g.
View Article and Find Full Text PDFAccessing a Diverse Set of Functional Red-Light Photoswitches by Selective Copper-Catalyzed Indigo -Arylation.
J Am Chem Soc
August 2024
Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Kita 21, Nishi 10, Kita-ku, Sapporo, Hokkaido 001-0021, Japan.
The ability to correlate the structure of a molecule with its properties is the key to the rational and accelerated design of new functional compounds and materials. Taking photoswitches as an example, the thermal stability of the metastable state is a crucial property that dictates their application in molecular systems. Indigos have recently emerged as an attractive motif for designing photoswitchable molecules due to their red-light addressability, which can be advantageous in biomedical and material applications.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!