A Palladium-catalyzed α-arylation of sulfonamides with aryl chlorides is presented. A Buchwald type precatalyst formed with Kwong's indole-based ligand enabled this transformation to be compatible with a large variety of methyl sulfonamides and aryl chlorides in good to excellent yields. Importantly, under the optimized reaction conditions, only mono-arylated products were observed. This method has been applied to the efficient synthesis of sumatriptan, which is used to treat migraines.
Download full-text PDF |
Source |
---|---|
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5218594 | PMC |
http://dx.doi.org/10.1002/adsc.201600090 | DOI Listing |
ACS Catal
December 2024
Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States.
A Rh(III)-catalyzed sequential C-H bond addition to dienes and in situ formed aldimines was developed, allowing for the preparation of otherwise challenging to access amines with quaternary centers at the -position. A broad range of dienes were effective inputs and installed a variety of aryl and alkyl substituents at the quaternary carbon site. Aryl and alkyl sulfonamide and carbamate nitrogen substituents were incorporated by using different formaldimine precursors.
View Article and Find Full Text PDFWater Res
December 2024
CAS Key Laboratory of Urban Pollutant Conversion, Department of Environmental Science and Engineering, University of Science and Technology of China, Hefei 230026, China. Electronic address:
Heterotrophic nitrification, similar to autotrophic nitrification, involves key enzymes and reactive nitrogen intermediates during ammonia oxidation, which may influence antibiotic transformation. However, the interference between antibiotic transformation products from ammonia oxidation and secondary metabolites in heterotrophic nitrifiers makes antibiotic transformation pathways more complicated. In this work, we observe that the heterotrophic nitrifier Alcaligenes ammonioxydans HO-1 can effectively convert sulfonamide antibiotics.
View Article and Find Full Text PDFOrg Lett
January 2025
Technical Institute of Fluorochemistry, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China.
A three-component reaction of trifluoromethyl enones, phosphine oxides, and alcohols in water solution is developed. This defluorinative reaction occurs through a cascade process involving defluorophosphorylation, defluoroalkyloxylation, and defluoroheteroannulation, enabling the modular synthesis of furans with four distinct substituents: 2-alkyloxy, 3-trifluoromethyl, 4-phosphoryl, and 5-(hetero)aryl groups. Moreover, apart from alcohol substrates, the scope of nucleophiles could be further extended to phenols, azacycles, or sulfonamide.
View Article and Find Full Text PDFBiochem Pharmacol
December 2024
Center for Drug Discovery, Graduate School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan. Electronic address:
The discovery of new small-molecule inhibitors is essential to enhancing our understanding of biological events at the molecular level and driving advancements in drug discovery. Mitotic inhibitors have played a crucial role in development of anticancer drugs. Beyond traditional microtubule inhibitors, various inhibitors targeting specific mitotic factors have been developed.
View Article and Find Full Text PDFAcc Chem Res
January 2025
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan.
ConspectusSelective chemical modification of endogenous proteins in living systems with synthetic small molecular probes is a central challenge in chemical biology. Such modification has a variety of applications important for biological and pharmaceutical research, including protein visualization, protein functionalization, proteome-wide profiling of enzyme activity, and irreversible inhibition of protein activity. Traditional chemistry for selective protein modification in cells largely relies on the high nucleophilicity of cysteine residues to ensure target-selectivity and site-specificity of modification.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!