The first example of catalytic thiocarbonylation of aryl iodides using CO has been achieved employing a combination of PdCl and carbazole-derived phosphine ligands. Under mild conditions, a broad scope of aryl iodides were converted to the desired thioester products in the presence of aryl or alkyl thiols (33 examples, up to 96% yields). The choice of metal, ligands, and reductant were crucial for high efficiency and chemoselectivity. Moreover, this strategy provided an effective method for the late-stage functionalization of biorelevant molecules.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.3c00643 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Electrochemical Synthesis of 3-(Sulfonyl)quinol-4-ones from -Alkynyl--(formyl)anilides and Sulfinates.
Org Lett
December 2024
Organic Chemistry Department, Science Faculty, Patrice Lumumba Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya strasse, 6, 117198 Moscow, Russia.
Electrolysis of -alkynyl--(formyl)anilides and sodium sulfinates on graphite electrodes delivers biologically sound 3-(sulfonyl)quinol-4-ones with moderate to good yields. The reaction is carried out in an undivided cell in the presence of silver(I) oxide with potassium iodide or sodium tetrafluoroborate as the supporting electrolyte. The reaction tolerates variously substituted anilides as well as aryl and alkyl sulfinates.
View Article and Find Full Text PDFCurrent-Regulated Selective Nickel-Catalyzed Electroreductive Cross-Electrophile Carbonylation to β/γ-Hydroxy Ketones.
Angew Chem Int Ed Engl
December 2024
Xi'an Jiaotong University, School of Chemical Engineering & Technology, Xingqing Road 28, 710049, Xi'an, CHINA.
The nickel catalyzed multi-component cross-electrophile carbonylation which emerges as a powerful and efficient method for constructing diverse ketones has attracted increasing attention of organic chemists. However, the selectivity of this reaction poses a significant challenge. In this work, we have developed a current-regulated selective nickel-catalyzed electroreductive cross-electrophile carbonylation, which offers a direct convergent synthesis of β/γ-hydroxy ketones, which represent pivotal structural motifs found in numerous natural products, bioactive molecules, pharmaceutical compounds, and essential building blocks.
View Article and Find Full Text PDFAmphiphilic palladium NHC-complexes with chelating bis-NHC ligands based on imidazole-4,5-dicarboxylic acid: synthesis and catalysis in water.
Org Biomol Chem
December 2024
Alexander Butlerov Institute of Chemistry, Kazan Federal University, 18 Kremlevskaya Str., 420008 Kazan, Russia.
Efficient catalytic systems for various organic transformations in green solvents, especially water, are in great demand. Catalytically active bis-NHC complexes of palladium(II) based on imidazole-4,5-dicarboxylic acid with different lipophilicities were obtained. The synthesis of imidazolium salts was complicated by the formation of side products of nucleophilic substitution by iodide ions in the Menshutkin reaction involving alkyl iodides, which was successfully resolved by using alkyl tosylates.
View Article and Find Full Text PDFGold(I/III)-Catalyzed Sulfonylation of Aryl/Vinyl Iodides To Synthesize Aryl Sulfones.
J Org Chem
December 2024
School of Materials Science & Engineering, Beijing Institute of Technology, Beijing 100081, China.
A gold-catalyzed sulfonylation of aryl/vinyl iodides to synthesize aryl sulfones facilitated by the ligand-enabled Au(I)/Au(III) redox catalysis was developed. In the reaction, aryl sodium sulfinates or sulphinic acids can react smoothly with aryl/vinyl iodides to directly construct various aryl sulfones. The strong synthetic capabilities of sulfone synthesis are demonstrated by its easily available and handled reagents, good functional group compatibility, and late-stage application of complicated biomolecules.
View Article and Find Full Text PDFPalladium-Catalyzed Selective Carbonylation Reactions of -Phenylene Dihalides with Bifunctional ,-Nucleophiles.
Molecules
November 2024
Department of General and Inorganic Chemistry, University of Pécs, Ifjúság u. 6., H-7624 Pécs, Hungary.
Palladium-catalyzed carbonylation reactions of -phenylene dihalides were studied using aminoethanols as heterobifunctional ,-nucleophiles. The activity of aryl-iodide and -bromide as well as the chemoselective transformation of amine and hydroxyl functionalities were studied systematically under carbonylation conditions. Aminocarbonylation can be selectively realized under optimized conditions, enabling the formation of amide alcohols, and the challenging alkoxycarbonylation can also be proved feasible, enabling amide-ester production.
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!