Direct arylation and alkenylation of 1-substituted tetrazoles was achieved via Pd catalysis in the presence of CuI and Cs(2)CO(3). Unlike the related reactions of imidazoles and purines, phosphine ligand was necessary to prevent the intermediate tetrazolyl-Pd(II) species from fragmentation into the corresponding cyanamide. Various 1,5-disubstituted tetrazoles were prepared with good to excellent isolated yields.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1021/jo902180u | DOI Listing |
Proc Natl Acad Sci U S A
December 2024
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409.
J Org Chem
December 2024
Key Laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education, Hubei Key Laboratory of Bioinorganic Chemistry and Materia Medica, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology (HUST), 1037 Luoyu Road, Wuhan 430074, P. R. China.
Recently, metallaphotoredox-catalyzed alkene dicarbofunctionalization reactions have been extensively investigated. Most cases are related to alkyl-arylation processes by conjugate coupling of alkyl radical precursors and aryl electrophiles across alkenes. By contrast, reported examples of alkylvinylation by coupling of vinyl electrophiles are largely limited.
View Article and Find Full Text PDFChemistry
January 2025
Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstraße 21, Freiburg im Breisgau, 79104, Germany.
Reliable radical precursors are crucial for photocatalytic processes. In particular, heteroatom-stabilized radicals have attracted considerable research interest in photocatalysis. Among them, α-amino radicals have received the most attention, while the research on α-hydroxy radicals is much less developed.
View Article and Find Full Text PDFNat Commun
October 2024
Shanghai Key Laboratory of Molecular Engineering of Chiral Drugs, Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, 200240, Shanghai, P. R. China.
Org Lett
October 2024
College of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, China.
A nickel-catalyzed enantioselective cross-coupling for the synthesis of P-stereogenic phosphinamides has been developed. The asymmetric alkenylation and arylation of racemic H-phosphinamides using alkenyl and aryl bromides resulted in the formation of P-stereogenic N-phosphinyl compounds with good yields and high enantioselectivities. This method tolerates a variety of functional groups, and its applications are explored through scale-up reactions and product transformations.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!