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Palladium-catalyzed C-H acetoxylation reactions of 2-methoxyimino-2-aryl-acetates and acetamides have been developed. These transformations feature excellent regioselectivity, wide substrate scope, and moderate to good yields. The product can be easily converted into naturally unprecedented α-amino acids in excellent yields.
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http://dx.doi.org/10.1039/c1ob05887h | DOI Listing |
J Org Chem
September 2025
Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education), and Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha, Hunan 410081,
We herein report a palladium-catalyzed dearomative Heck/C(sp)-H activation/[4 + 2] decarboxylative cyclization of C2-tethered indoles. In this transformation, the alkylpalladium(II) species generated by indole dearomatization undergoes C-H activation to form ,-palladacycles, which are subsequently trapped by -bromobenzoic acids or cyclic β-bromoacrylic acids, enabling regio- and diastereoselective construction of hexacyclic and octocyclic fused indolines with a broad substrate scope.
View Article and Find Full Text PDFChem Pharm Bull (Tokyo)
September 2025
Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aoba, Aramaki, Aoba-ku, Sendai 980-8578, Japan.
In this study, a palladium-catalyzed, amide-directed C-H acetoxylation of cubanes has been developed. The ortho positions of the amide directing group on cubanes were selectively acetoxylated without any stoichiometric strong bases. The number (1-3) of acetoxy groups introduced was determined by the amount of PhI(OAc) used.
View Article and Find Full Text PDFACS Omega
August 2025
Departamento de Química, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, Belo Horizonte, Minas Gerais 31270-901, Brazil.
A Pd-mediated C-H activation methodology was developed for the direct arylation of quinoidal skeletons, both by means of homogeneous catalysis and heterogeneous catalysis using metal-decorated carbon nanotubes, enabling the direct functionalization of quinones in moderate to excellent yields. The derivatives obtained were tested against trypomastigote forms of , showing promising biological activity.
View Article and Find Full Text PDFOrg Lett
August 2025
Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
Chemoselective incorporation of hydrogen isotopes is a useful tool for drug discovery and mechanistic investigation. While late-stage C-H functionalization via hydrogen isotope exchange (HIE) offers a straightforward route to isotopically labeled compounds, existing methods often use deuterated solvents which are not feasible for tritium labeling. Hence, direct use of simple deuterium gas for isotopic labeling is highly desirable.
View Article and Find Full Text PDFJ Am Chem Soc
September 2025
State Key Laboratory of Bioinspired Interfacial Materials Science, MOE Key Laboratory of Geriatric Diseases and Immunology, Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China.
Amide units and relative carbonyl families such as ureas and their derivatives are central important backbones of numerous compounds with activities of relevance to biology or medicinal chemistry. Driven by their prevalence, a general technology that enables sustainable amide-unit synthesis should afford new opportunities for chemical innovation. Generally, stoichiometric quantities of activating reagents, (tri)phosgene and its derivatives, or CO are commonly used in the literature to construct such scaffolds, which represent the drawbacks of these approaches.
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