Herein, we report a method for the regioselective alkylation and phosphonation of quinoline C4-H via a BH-mediated nucleophilic addition of Turbo Grignard reagents and phosphine oxide anions to quinolines bearing different substituents, affording the 4-alkyl and 4-phosphoryl quinolines and tetrahydroquinolines after one-pot oxidation or reduction. The results indicate that coordination of the BH group can activate substrates toward a potential 1,4-dearomative addition and subtly control the regioselectivity by preventing the 1,2-dearomative addition.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.4c04713 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Metal-Organic Frameworks with Phosphonate Monoester Linkers for Catalytic C(sp)-H Borylation of Alkenes.
Inorg Chem
January 2025
State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian 350002, China.
An isoreticular metal-organic framework (MOF) series was constructed from nickel or cobalt nodes, phosphonate monoester, and bipyridine linkers. The cobalt-containing MOFs were found to catalyze the dehydrogenative C-H borylation of alkenes under mild conditions. This process selectively generates vinyl boronate without the formation of alkyl boronate byproducts and is insensitive to air, enabling large-scale preparation of the target products with isolated yields of over 80%.
View Article and Find Full Text PDFTrinuclear Borane (BH)-Mediated Selective C4-H Alkylation and Phosphonation of Quinolines and Tetrahydroquinolines.
Org Lett
January 2025
College of Chemistry, Zhengzhou University, Zhengzhou, Henan 450001, China.
Herein, we report a method for the regioselective alkylation and phosphonation of quinoline C4-H via a BH-mediated nucleophilic addition of Turbo Grignard reagents and phosphine oxide anions to quinolines bearing different substituents, affording the 4-alkyl and 4-phosphoryl quinolines and tetrahydroquinolines after one-pot oxidation or reduction. The results indicate that coordination of the BH group can activate substrates toward a potential 1,4-dearomative addition and subtly control the regioselectivity by preventing the 1,2-dearomative addition.
View Article and Find Full Text PDFBase-Promoted 1,4-Difunctionalization of [60]Fullerene with H-Phosphonates and Alkyl Bromides.
Org Lett
December 2024
Department of Chemistry, Anhui University, Hefei, Anhui 230601, People's Republic of China.
The DBU-promoted three-component coupling reaction of H-phosphonates, [60]fullerene, and alkyl bromides has been developed as a facile and efficient protocol for the one-pot synthesis of various 1,4-(phosphonyl)(organo)[60]fullerenes. This method exhibits high regioselectivity at the 1,4-position on the [60]fullerene core and features a metal-free nature, easy operation, low cost, and a wide range of substrates.
View Article and Find Full Text PDFCross-bridged cyclam derivatives with bis(phosphinate) and phosphinate-phosphonate pendant arms (cb-BPC) as chelators for copper radioisotopes.
Org Biomol Chem
November 2024
Department of Inorganic Chemistry, Faculty of Science, Charles University in Prague, Hlavova 2030, 128 40 Prague, Czech Republic.
Copper radioisotopes can be used for imaging as well as for therapy and, thus, can form ideal theranostic pairs. The Cu(II) complexes of cross-bridged cyclam (cb-cyclam) derivatives are considered to be highly stable . However, the complexes are mostly formed under harsh conditions not compatible with sensitive biomolecules.
View Article and Find Full Text PDFLate-stage (radio)fluorination of alkyl phosphonates via electrophilic activation.
Nat Commun
November 2024
State Key Laboratory of Vaccines for Infectious Diseases, Center for Molecular Imaging and Translational Medicine, School of Public Health, Xiamen University, Xiamen, Fujian, China.
Constructing organic fluorophosphines, vital drug skeletons, through the direct fluorination of readily available alkyl phosphonates has been impeded due to the intrinsic low electrophilicity of P and the high bond energy of P═O bond. Here, alkyl phosphonates are electrophilically activated with triflic anhydride and N-heteroaromatic bases, enabling nucleophilic fluorination at room temperature to form fluorophosphines via reactive phosphine intermediates. This approach facilitates the late-stage (radio)fluorination of broad dialkyl and monoalkyl phosphonates.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!