The magnesiation of halogenated aromatic and heteroaromatic carboxylic acids is accomplished by their treatment with MeMgCl in the presence of LiCl and subsequent reaction with i-PrMgCl.LiCl; the resulting double-magnesiated species react with a variety of electrophiles in up to 97% yield.

Download full-text PDF

Source
http://dx.doi.org/10.1039/b618923gDOI Listing

Publication Analysis

Top Keywords

aromatic heteroaromatic
8
heteroaromatic carboxylic
8
carboxylic acids
8
halogen-magnesium exchange
4
exchange unprotected
4
unprotected aromatic
4
acids magnesiation
4
magnesiation halogenated
4
halogenated aromatic
4
acids accomplished
4

Similar Publications

Fluorescent Macrocyclic Arenes: Synthesis and Applications.

Angew Chem Int Ed Engl

January 2025

Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institution Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China.

Fluorescent macrocyclic arenes have attracted increasing interest in macrocyclic and supramolecular chemistry due to their exceptional photophysical properties and versatile applications. Classical macrocyclic arenes modified with fluorescent groups at the upper or bottom rims have long provided valuable platforms across various fields. Recently, a large number of novel fluorescent macrocyclic arenes directly composed of polycyclic aromatic or heteroaromatic building blocks including naphthalene, anthracene, tetraphenylethene, pyrene, fluorene, carbazole, acridan, phenothiazine, coumarin, triphenylamine, benzothiadiazole and so on, have been reported, and they have shown specific fluorescent property, and also exhibited broad applications in molecular recognition, sensing, bioimaging and functional materials.

View Article and Find Full Text PDF

Unlabelled: We have developed novel and sustainable homogeneous catalysts employing Glutamic acid (Glu) as a biodegradable and eco-friendly organocatalyst for the synthesis of -(4-oxo-2-phenyl-1,2-dihydroquinazolin-3(4)-yl)isonicotinamide derivatives (-) via multicomponent reactions (MCRs) of isatoic anhydride, isoniazid and heteroaromatic/aromatic aldehyde in ethanol on oil bath stirring at 60 °C. Selected final product homogeneity was examined by various spectroscopic techniques such as C-, H- NMR, FT-IR and LC-MS. For the first time, herein investigated electrochemical behavior of selected derivatives (-) using cyclic voltammetry method.

View Article and Find Full Text PDF

Functionalization of Pyridines at the C4 Position via Metalation and Capture.

Angew Chem Int Ed Engl

January 2025

Department of Chemistry, Texas A&M University, PO Box 30012, College Station, TX 77842-30012.

The functionalization of pyridines at positions remote to the N-atom remains an outstanding problem in organic synthesis. The inherent challenges associated with overriding the influence of the embedded N-atom within pyridines was overcome using n-butylsodium, which provided an avenue to deprotonate and functionalize the C4-position over traditionally observed addition products that are formed with organolithium bases. In this work, we show that freshly generated 4-sodiopyrdines could undergo transition metal free alkylation reactions directly with a variety of primary alkyl halides bearing diverse functional groups.

View Article and Find Full Text PDF

Carboxylations of (Hetero)Aromatic C-H Bonds Using an Alkyl Silyl Carbonate Reagent.

Org Lett

January 2025

Department of Biophysical Chemistry, Graduate School of Pharmaceutical Science, Tohoku University, AobaSendai 980-8578, Japan.

In this paper, we report that the use of an alkyl silyl carbonate reagent combined with CsF and 18-crown-6 facilitates efficient direct carboxylations of (hetero)aromatic C-H bonds. This system also enables benzylic carboxylation of a toluene derivative and double carboxylation of methyl heteroarene. The carbonate reagent is characterized by its ease of handling and storage.

View Article and Find Full Text PDF

Electrophilic aromatic substitution at the C5 position of isoxazolines and construction of a new quaternary carbon center were achieved in this paper. This is the first report of carbon-carbon (C-C) bond formation onto isoxazoline without compromising the ring structure. Various aromatics including heteroaromatics gave the desired products in good yields, especially aromatics bearing electron-donating groups.

View Article and Find Full Text PDF

Want 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!