We report a one-pot synthesis of aryl carboxylic acids utilizing HCOOH as a CO surrogate with low Pd-catalyst loading. This operationally simple and scalable method does not require use of a high-pressure reactor, two-chamber reaction vessel, phosphine ligand, or base and proceeds in a relatively short amount of time at ambient temperature. Notably, halides, including iodo and bromo groups, and nitro groups remain intact under these mild reaction conditions. This methodology has been successfully applied to synthesizing C-labeled aryl carboxylic acids with satisfactory yields.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1039/d4cc04758c | DOI Listing |
Angew Chem Int Ed Engl
January 2025
University of Basel, Department of Chemistry, St. Johanns-Ring 19, 4056, Basel, SWITZERLAND.
Despite the growing importance of planar chiral macrocyclophanes owing to their unique properties in different areas of chemistry, methods that are effective in controlling their planar chirality are restricted to certain molecular scaffolds. Herein, we report the first Pd(0)-catalyzed enantioselective intermolecular C-H arylation that induces planar chirality by installing bulky aryl groups through dynamic kinetic resolution (DKR). A computer-assisted approach allowed a fine-tuning of the structure of the employed chiral bifunctional phosphine-carboxylate ligands to achieve high enantioselectivities.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
Department of Chemistry, School of Advanced Sciences, Vellore Institute of Technology, Vellore, Tamil Nadu-632014, India.
A porphyrin comprising a carboxyl-functionalized pyridine moiety was synthesized and characterized using H NMR, C NMR, FT-IR, powder-XRD, BET, ICP-MS, SEM and EDAX. The proton level (H = 1.19) and energy band gap (1.
View Article and Find Full Text PDFCurr Org Synth
January 2025
Stem Cells Technology Research Center, Shiraz University of Medical Sciences, Shiraz, Iran.
Introduction: The development of efficient and sustainable catalytic methodolo-gies has garnered considerable attention in contemporary organic synthesis.
Methods: Herein, we present a novel approach employing the Cu@DPP-SPION catalyst for the synthesis of ethyl 4-(aryl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate derivatives. This versatile catalytic system incorporates copper nanoparticles supported on 4-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)benzoic acid-functionalized superparamagnetic iron oxide nanoparticles (SPIONs).
Angew Chem Int Ed Engl
January 2025
Nanjing University, Chemistry, Xianlin 163Hao, Nanjing 210023, 210023, Nanjing, CHINA.
The simple and efficient conversion of carboxylic acids into structurally diverse organic molecules is highly desirable in chemical synthesis. This review covers recent developments in photocatalytic methodology for late-stage transformations of complex carboxylic acids and their derivatives enabled by radical decarboxylation and deoxygenation, highlighting some representative and significant contributions in this field. These advancements are categorized based on the reactivity patterns exhibited by the carboxylic acids.
View Article and Find Full Text PDFChem Sci
January 2025
University of Regensburg, Institute of Inorganic Chemistry 93040 Regensburg Germany
We present a photocatalytic protocol for the -arylation of carboxylic acids using nickel complexes bearing C8-pyridyl xanthines. Our studies suggest that the underlying mechanism operates independently of external photosensitizers. Stoichiometric experiments and crystallographic studies characterize the catalytically relevant Ni complexes.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!