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A broad range of 1,10-phenanthroline substrates was efficiently C-H functionalised, providing rapid, gram-scale access to substituted heteroaromatic cores of broad utility. Furthermore, this C-H functionalisation pathway was extended to the synthesis of previously inaccessible, ultra-soluble, 2,9-bis-triazinyl-1,10-phenanthroline (BTPhen) ligands for advanced nuclear fuel cycles.
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http://dx.doi.org/10.1039/c7cc03903d | DOI Listing |
Org Lett
September 2025
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India.
A transition-metal-free ring opening of bicyclo[1.1.0]butanes (BCBs) using hydroperoxides as nucleophiles in hexafluoroisopropanol (HFIP) resulting in the diastereoselective synthesis of peroxycyclobutanes under mild conditions with a broad scope is demonstrated.
View Article and Find Full Text PDFJ Am Chem Soc
September 2025
Institute of Integrated Research, Institute of Science Tokyo, 4259 Nagatsuta, Midori-ku, Yokohama 226-8501, Japan.
Upgrading methane to value-added chemicals is significant but still challenging. Well-designed catalysts are required to activate methane. Extensive efforts have been dedicated to the catalytic conversion of methane over transition-metal-containing catalysts.
View Article and Find Full Text PDFJ Org Chem
September 2025
College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, People's Republic of China.
We herein report the Minisci-type redox-neutral decarboxylative hydroxyalkylation of heteroarenes under photocatalyst- and transition-metal-free conditions. This methodology tolerates various functional groups that can be subsequently elaborated. Upon absorption of photons, the excited state of the α-oxocarboxylic acid forms an acyl radical, which adds to the protonated heteroarene to give the desired product after a spin center shift (SCS), reduction, and deprotonation.
View Article and Find Full Text PDFOrg Lett
September 2025
Jiangxi Province Key Laboratory of Natural and Biomimetic Drugs Research, College of Chemistry and Materials, Jiangxi Normal University, Nanchang 330022, China.
The annulation reaction of β-methyl enaminones with alkynones leading to the synthesis of methylene-functionalized 1,2-dihydropyridines (1,2-DHPs) has been realized. In the presence of only CsCO, 1,2-DHPs have been synthesized with a broad scope and generally high efficiency via the novel transformation of the γ-C(sp)-H bond in enaminones. In addition, the application of the method has been demonstrated by the one-step transformation of the 1,2-DHP products into fused tricyclic scaffolds featuring an indole-pyridine hybrid via dual C-H activation.
View Article and Find Full Text PDFJ Phys Chem A
September 2025
Institut für Organische Chemie, Eberhard Karls Universität Tübingen, Auf der Morgenstelle 18, Tübingen 72076, Germany.
Carbenes are promising reagents for the transition metal-free activation of molecular hydrogen. Depending on their multiplicity and electron configuration, carbenes can access different hydrogenation reaction mechanisms, with singlet carbenes usually leading to geminal hydrogenation products a π-approach trajectory. Our group has recently prepared 1-iodopyridine-2-ylidene, , introducing a new class of singlet -heterocyclic carbenes featuring σ/σ* instead of the usually encountered σ/π frontier orbitals.
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