Trialkylstannanes are versatile precursors for chemical transformations, including radiolabeling with a variety of halogens, particularly iodine. In the present work a convenient, Pd-mediated stannylation method is presented that can be performed in an open flask. The method is selective for aryl iodides allowing selective stannylations in the presence of other halogen atoms. The reaction conditions are mild, making the method compatible with chemically sensitive bioactive compounds.
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http://dx.doi.org/10.1016/j.bmcl.2015.02.055 | DOI Listing |
Org Lett
January 2025
Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
Dehydrophenylalanine has a characteristic unsaturated double bond that makes it indispensable in the context of peptides and proteins. In this study, we report the Pd-catalyzed C(sp)-H arylation of dehydroalanine-containing peptides with arylthianthrenium salts under mild and base free conditions, which provides efficient access to dehydrophenylalanine-containing peptides. This approach enables the efficient coupling of different drug scaffolds and bioactive molecules to the peptides.
View Article and Find Full Text PDFOrg Lett
January 2025
Hefei National Research Center for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, People's Republic of China.
A three-component coupling strategy for 1,4-dicarbofunctionalization of 1,3-butadiene with C-H bearing substrates has been developed using photoinduced Pd catalysis, with aryl bromide serving as the hydrogen atom transfer (HAT) reagent. This photocatalytic coupling process achieves functionalized oxindole motifs in good yield and regioselectivity under mild reaction conditions. The versatility and synthetic utility of this method are demonstrated through the addition of a variety of C-H-bearing partners and various oxindole substrates to both substituted and unsubstituted butadiene.
View Article and Find Full Text PDFJ Org Chem
January 2025
Applied Organic Chemistry Group, Chemical Science and Technology Division, CSIR-North East Institute of Science and Technology, Jorhat 785006, India.
A synthetic strategy of a palladium-catalyzed cascade annulation reaction followed by aerial oxidation was designed to construct 6-benzo[c]chromene scaffolds. Various 6-benzo[c]chromenes were synthesized under mild reaction conditions using easily accessible -QMs and commercially available -hydroxyarylboronic acids. One of the synthesized chromenes has been ambiguously confirmed by single-crystal XRD analysis.
View Article and Find Full Text PDFJ Org Chem
January 2025
School of Chemistry and Chemical Engineering, Linyi University, The middle of Shuangling Road, Linyi, Shandong 276000, People's Republic of China.
Two novel Pd-catalyzed protocols for the controllable synthesis of benzo[]furo[2,3-]azepines and furo[3,2-]indoles have been developed by intermolecular oxidative annulation of 2-(furan-2-yl)anilines and propargyl carbonates versus intramolecular C-H amination reactions. These two protocols feature great scalability, functional group tolerance, and relatively mild reaction conditions. Notably, the robust methodologies could also provide valuable opportunities for assembling azepine-fused benzothiophene, indole-fused benzothiophene, and indole-fused benzimidazole, which may have potential applications in the synthesis of related pharmaceuticals or polymeric materials.
View Article and Find Full Text PDFJ Org Chem
December 2024
School of Traditional Chinese Medicine, Southern Medical University, Guangzhou 510515, P. R. China.
To date, a general approach for the direct α-acyloxylation of cyclic 1,3-dicarbonyls remains challenging. Herein, we report a Pd-catalyzed α-acyloxylation of cyclic 1,3-dicarbonyl-derived hypervalent iodine compounds with highly abundant carboxylic acids. Our approach utilizes a commercially available Pd(OAc) catalyst, which exhibits mild reaction conditions, scalability, operational simplicity, and robustness against moisture and air.
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