In this report, we disclose our findings regarding the remarkable effect of a low-level impurity found in the solvent used for a ruthenium-catalyzed direct arylation reaction. This discovery allowed for the development of a robust and high-yield arylation protocol that was demonstrated on a multikilogram scale using carboxylate as the cocatalyst. Finally, a practical, scalable, and chromatography-free synthesis of the biaryl core of Anacetrapib is described.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/jo1018574 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Copper(I)-Catalyzed Intramolecular Tandem Acylation/-Arylation under Mild Conditions: Synthesis of Benzofuro[3,2-]quinolin-6(5)-ones and G-Quadruplex-Targeting Analogues.
J Org Chem
December 2024
Institute of BioPharmaceutical Sciences, National Sun Yat-sen University, No. 70, Lien-hai Road, Kaohsiung 804201, Taiwan.
This paper presents a copper(I)-catalyzed intramolecular tandem acylation/-arylation of methyl 2-[2-(2-bromophenyl)acetamido]benzoates for the synthesis of benzofuro[3,2-]quinolin-6(5)-ones under mild conditions. The combination of CuI, 1,10-phenanthroline, and KCO in DMSO was found to be the optimal reaction condition, producing the target products in high yields (84-99%) at 70 °C for 16 h. The tandem reaction was applicable to substrates bearing halo, electron-withdrawing, and electron-donating groups at their phenyl moieties with a broad substrate scope.
View Article and Find Full Text PDFAlkali-Cation-Selective Arylation Promoted by Ion Recognition of Foldamers.
Org Lett
December 2024
State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, China.
To explore alkali-cation selectivity at the chemical reaction level, in this work, we for the first time focused on the different behaviors of potassium and sodium ions in intra- and intermolecular arylation. We prepared a series of aromatic foldamers based on pyridine/oxadiazole alternating sequences as the catalysts for the arylation. Our studies revealed that foldamers can selectively recognize K over Na and the interactions between foldamers and K drive the arylation with a significant yield.
View Article and Find Full Text PDFIntramolecular C-H arylation of pyridine derivatives with a palladium catalyst for the synthesis of multiply fused heteroaromatic compounds.
Beilstein J Org Chem
December 2024
Department of Chemical Science and Engineering, Kobe University, 1-1 Rokkodai, Nada, Kobe 657-8501, Japan.
The C-H arylation of 2-quinolinecarboxyamide bearing a C-Br bond at the -aryl moiety is carried out with a palladium catalyst. The reaction proceeds at the C-H bond on the pyridine ring adjacent to the amide group in the presence of 10 mol % Pd(OAc) at 110 °C to afford the cyclized product in 42% yield. The yield is improved to 94% when the reaction is performed with PPh as a ligand of palladium.
View Article and Find Full Text PDFUnveiling the molecular mechanism of Mn and Zn-catalyzed Ullmann-type C-O cross-coupling reactions.
Phys Chem Chem Phys
December 2024
Department of Chemistry, CMS College Kottayam (Autonomous) Mahatma Gandhi University, Kottayam, Kerala, 686001, India.
A detailed theoretical study delving into the molecular mechanisms of the Ullmann-type -arylation reactions catalyzed by manganese and zinc metal ions has been investigated with the aid of the density functional theory (DFT) method. In contrast to the redox-active mechanisms proposed for classical Ullmann-type condensation reaction, a redox-neutral mechanism involving σ-bond metathesis emerged as the most appealing pathway for the investigated high-valent Mn(II) and Zn(II)-catalyzed -arylation reactions. The mechanism remains invariant with respect to the nature of the central metal, ligand, base, This unusuality in the mechanism has been dissected by considering three cases: ligand-free and ligand-assisted Mn(II)-catalyzed -arylation reaction and ligand-assisted Zn(II)-catalyzed -arylation reactions.
View Article and Find Full Text PDFBase-Promoted Sulfur Arylation of Sulfenamides to Oxonium Aryne Precursors: Chemoselective Synthesis of Sulfilimines and -Sulfanylanilines.
J Org Chem
December 2024
School of Pharmacy, Guangdong Pharmaceutical University, Guangzhou 510006, P. R. China.
In this study, a metal-free and efficient method for the synthesis of sulfilimines and -sulfanylanilines in high yields with excellent chemoselectivities from oxonium aryne precursors with sulfenamides has been developed. This method features mild reaction conditions, simple operations, a general substrate scope, and good tolerance of functional groups. In addition, scale-up synthesis, related applications, and preliminary mechanistic explorations were also investigated.
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!