An efficient Pd-catalyzed amidation of 1,3-diketones has been developed using carbon monoxide and organic azides. This reaction provides a step-economic approach to produce β-ketoamides from readily available compounds under mild ligand-, oxidant-, and base-free conditions. The mechanistic studies showed that the reaction occurred through an in situ generated isocyanate intermediate.
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http://dx.doi.org/10.1039/d0cc04565a | DOI Listing |
Angew Chem Int Ed Engl
January 2025
University of Melbourne, School of Chemistry, 30 Flemington Rd., VIC 3095, Parkville, AUSTRALIA.
Palladium(II)-catalyzed C-H functionalization has attracted considerable attention as a pathway to late-stage modification of peptides. Herein, we report the Pd-catalyzed C(sp3)-H arylation of peptides directed by an amidoxime ether, which can be easily incorporated into peptides at any amide bond. Site- and stereoselective arylation of peptides has been achieved, including an unprecedented example of C-H arylation of an internal residue.
View Article and Find Full Text PDFBioconjug Chem
December 2024
Department of Chemistry, Gwangju Institute of Science and Technology (GIST), Gwangju 61005, Republic of Korea.
The dsDNA-selective fluorescent-dye-based DNA damage assay was developed for DNA-encoded library (DEL) synthesis. For the various DEL synthesis conditions, the assay was validated through cross-checking with high-performance liquid chromatography (HPLC) analysis, and the fact was confirmed that the usage of a specific ratio of organic solvent can critically induce DNA damage. Also, the applicability of the assay was confirmed through the screening of the DNA-damaging condition of the on-DNA amide coupling reaction and Pd-catalyzed on-DNA -arylation reaction.
View Article and Find Full Text PDFChempluschem
December 2024
Department of Chemical and Environmental Process Engineering, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, Műegyetem rkp. 3., H-1111, Budapest, Hungary.
The palladium-catalyzed aminocarbonylation is one of the most effective methods for the synthesis of carboxamides having great importance. Replacing fossil-based organic solvents in this routinely used catalytic protocol with biomass-derived media is crucial for developing environmentally safe alternatives and towards sustainability considerations. In this study, the open-chain derivatives of bio-originated substance γ-valerolactone i.
View Article and Find Full Text PDFJ Org Chem
December 2024
Department of Chemistry, Rutgers University, 73 Warren Street, Newark, New Jersey 07102, United States.
The Suzuki-Miyaura biaryl cross-coupling is the pivotal technology for carbon-carbon coupling in pharmaceutical, polymer, and agrochemical fields. A long-standing challenge has been the development of efficient precursors for the decarbonylative cross-coupling of amide bonds. Herein, we report a highly chemoselective palladium-catalyzed Suzuki-Miyaura cross-coupling of -mesyl amides for the synthesis of biaryls by a tandem N-C(O)/C-C bond activation with high selectivity for decarbonylative cleavage.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
Institut des Biomolécules Max Mousseron, Univ Montpellier, CNRS, ENSCM, Montpellier, France.
Since the discovery of penicillin, the forerunner of the most widely used class of antibiotics ( β-lactams), natural compounds and their derivatives represented a major source of antibacterial therapeutic products whose availability enabled modern medical practices (invasive surgery, organ transplant, .). However, the relentless emergence of resistant bacteria is challenging the long-term efficacy of antibiotics, also decreasing their economic attractiveness for big pharma, leading to a significant decay in antibacterial development in the 21 century and an increased use of last-resort drugs such as carbapenems or colistin.
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