Tetraphenylenes not only are theoretically and experimentally interesting but also have potential applications in a variety of fields such as materials science, supramolecular chemistry, and asymmetric catalysis. A facile and efficient approach is reported for the syntheis of tetraphenylene and its derivatives from 2-iodobiphenyls via Pd-catalyzed C-H activation. A range of substituted tetraphenylenes can be synthesized using this method, and the reaction can be performed on gram scale with relatively high efficiency, demonstrating its practical utility. This novel approach provides easy access to tetraphenylenes and should facilitate research on the application of this type of fascinating molecules.
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http://dx.doi.org/10.1021/acs.orglett.6b00641 | 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 PDFChemistry
January 2025
Key Laboratory of Radiopharmaceuticals, Ministry of Education, College of Chemistry, Beijing Normal University, Beijing, 100875, China.
Optically pure monosubstituted [n]paracyclophanes are promising candidates for material synthesis, asymmetric catalysis, and drug discovery. Thus far, only a few catalytic asymmetric synthesis processes have been reported for assessing these strained atropisomers. In this study, we describe a highly enantioselective synthesis of monosubstituted [n]paracyclophanes by combining desymmetrization and kinetic resolution.
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 PDFAngew Chem Int Ed Engl
January 2025
School of Chemistry, The University of Melbourne, Victoria, 3010, 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(sp)-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 unprecedented functionalization of internal residues of native peptides.
View Article and Find Full Text PDFAcc Chem Res
January 2025
Department of Chemistry and Chemistry Institution for Functional Materials, Pusan National University, Busan 46241, Republic of Korea.
ConspectusControlling selectivity through manipulation of reaction intermediates remains one of the most enduring challenges in organic chemistry, providing novel solutions for selective C-C π-bond functionalization. This approach, guided by activation principles, provides an effective method for selective functional group installation, enabling direct synthesis of organic molecules that are inaccessible through conventional pathways. In particular, the selective functionalization of N-conjugated allenes and alkynes has emerged as a promising research focus, driven by advances in controlling reactive intermediates and activation strategies.
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