Deep-sea Diels-Alder: The asymmetric organocatalytic Diels-Alder reaction of cyclohexenones with aromatic nitroolefins can be carried out in seawater and brine. The reaction proceeds by an in situ enamine activation involving a one-step concerted addition pathway (see scheme).
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http://dx.doi.org/10.1002/anie.200900269 | DOI Listing |
Chemistry
December 2024
RGIPT: Rajiv Gandhi Institute of Petroleum Technology, Department of Sciences and Humanities, Faculty of Chemistry, INDIA.
Herein, we have demonstrated the design and synthesis of a novel Ni-immobilized MOF as heterogeneous catalyst for the dehydrogenation of N-heterocycles. A series of five and six-member N-heteroarenes bearing one or more heteroatoms were synthesized in up to 98% yield (> 33 examples). Late stage functionalization to the synthesis of b-glucuronides inhibitor, antimalarial drug quinine, and the nonsteroidal anti-inflammatory drug (NSAID) indomethacin were obtained under milder reactions conditions.
View Article and Find Full Text PDFChemMedChem
November 2024
Department of Chemistry of Bioactive Nitrogen-Containing Heterocyclic Bases, V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, Academika Kukharya Str. 1, 02094, Kyiv, Ukraine.
Chem Commun (Camb)
November 2024
Institute of Nano Science and Technology, Sector-81, Mohali 140306, Punjab, India.
We have developed two triazole-based covalent organic polymers (COPs) with donor-acceptor motifs. The keto-enriched COP demonstrated exceptional oxygen activation electrochemical stimuli, driven by strong push-pull interactions. studies and DFT calculations confirmed the critical role of enamine carbon positive charges in enhancing performance, setting new benchmarks in COP design.
View Article and Find Full Text PDFOrg Lett
November 2024
College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China.
A photoinduced three-component radical addition-aminalization cascade was accomplished, enabling rapid assembly of a wide range of densely functionalized γ-lactams. Key to this transformation is the electron-donor-acceptor (EDA) generation of enamine and in situ trapping of an iminium intermediate with bromodifluoroacetamide. This rationally designed protocol fully takes advantage of the polarity crossover (enamine-iminium) in the process, providing the modular assembly of previously inaccessible scaffolds.
View Article and Find Full Text PDFJ Org Chem
November 2024
Chimie ParisTech, PSL University, CNRS, Institute of Chemistry for Life and Health Sciences, 75005 Paris, France.
Despite conceptual breakthroughs in dual photoredox- and nickel-catalyzed arylation of radicals, the approach remains largely limited to localized C-centered radicals. Here, we extend it to allylic radicals, focusing on -allyl heterocycles. Using [Ir(dF(CF)ppy)(dtbbpy)]PF and NiCl(dtbbpy) under visible light, we achieve regioselective γ-amino radical arylation, yielding enamines in good yields.
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