Cross-dehydrogenative coupling between 3-hydroxycarbazoles and 2-naphthols has been achieved by using a mesoporous silica-supported oxovanadium catalyst.
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http://dx.doi.org/10.1039/d1ra07723f | DOI Listing |
Chem Commun (Camb)
January 2025
Department of Chemistry, Indian Institute of Technology Delhi, Hauz Khas, New Delhi, 110016, India.
We demonstrate the participation of cobalt in a photoinduced ligand-to-metal charge transfer process, which leads to the formation of ligand-based radical species and enables both homo and hetero cross-dehydrogenative coupling of indoles with decent yield at room temperature. This photo-induced LMCT process is substantiated by a series of mechanistic investigations.
View Article and Find Full Text PDFJ Org Chem
January 2025
Department of Chemistry, Birla Institute of Technology and Science Pilani, Pilani Campus, Rajasthan 333031, India.
A convenient and efficient transition-metal-free method has been developed for the C(sp)-H alkoxylation/aryloxylation of 1,4-quinones by direct cross-dehydrogenative coupling with readily available alcohols and phenols in the presence of TEMPO under simple and mild conditions. The method allowed the installation of a wide range of alkoxy/aryloxy groups, exhibited high functional group tolerance, showed a broad substrate scope, afforded good to excellent yields of products in a simple one-pot operation, and could be performed on a gram scale. Mechanistic investigation indicated the involvement of the radical pathway.
View Article and Find Full Text PDFACS Omega
December 2024
N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, 47 Leninsky prosp., Moscow 119991, Russian Federation.
The electrochemically induced reaction between alkenes, bearing an allylic hydrogen atom, and -hydroxyphthalimide was investigated. Cross-dehydrogenative C-O coupling with phthalimide--oxyl radical, derived from -hydroxyphthalimide, occurs instead of oxidation of the allylic site, with the formation of a carbonyl group or functionalization of the double C=C bond. The discovered transformation proceeds in an undivided electrochemical cell equipped with a carbon felt anode and a platinum cathode.
View Article and Find Full Text PDFInorg Chem
January 2025
Departamento de Química Inorgánica, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), Facultad de Ciencias, Universidad de Zaragoza - CSIC, 50009 Zaragoza, Spain.
An active catalytic system for the cross-dehydrogenative coupling (CDC) of a wide range of secondary amines with silanes is reported. The iridium(III) derivatives [Ir(H)(X)(κ-NSi)(L)] (NSi = {4,8-dimethylquinoline-2-yloxy}dimethylsilyl; L = coe, X = Cl, ; L = coe, X = OTf, ; L = PCy, X = Cl, ; L = PCy X = OTf, ), which are stabilized by a weak yet noticeable Ir···H-C agostic interaction between the iridium and one of the C-H bonds of the 8-Me substituent of the NSi ligand, have been prepared and fully characterized. These species have proven to be effective catalysts for the CDC of secondary amines with hydrosilanes.
View Article and Find Full Text PDFChempluschem
November 2024
Institute of Chemical Engineering, Ural Federal University, 19 Mira Str., 620062, Ekaterinburg, Russian Federation.
Azoloazine derivatives are known as promising small molecules that are potentially able to counteract a broad spectrum of RNA viruses including SARS-CoV-2. However, a pool of synthetic pathways to provide convenient structural modification of such compounds without de novo construction of the heterocyclic scaffold is rather limited so far. This work proposes an approach to the direct C(sp)-H functionalization of azolopyrimidine substrates with aromatic thiol residues, mediated by the iodine/persulfate reagent system.
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