A metal-free BF·OEt catalyzed direct decarbonylative arylation of diazoamides with readily accessible aryl aldehydes under an open-air atmosphere was developed to afford 3-aryloxindoles 1,2-aryl migration with high selectivity. The reaction offers an efficient pathway for 3-arylation of diazoamides under relatively mild conditions, which shows a high level of functional group tolerance of both electron-donating and electron-withdrawing groups with a broad substrate scope. 3-Aryloxindoles were also obtained by a substituent-controlled chemo- and site-selective C-H bond functionalization of unprotected salicylaldehyde derivatives.
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http://dx.doi.org/10.1039/d2ob00003b | DOI Listing |
Planta
January 2025
School of Life Science and Technology, Wuhan Polytechnic University, Wuhan, 430023, China.
Ginsenosides R2 and F2 are key active components of Panax japonicus var. major which exhibit a wide range of pharmacological effects. However, few UDP-glycosyltransferases (UGTs) involved in Rh2 and F2 biosynthesis have been identified.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
Indian Institute of Chemical Technology, Organic Synthesis and Process Chemistry, Uppal Road, 500607, Hyderabad, INDIA.
Catalytic hydrocupration of unsaturated carbon-carbon bonds to generate organometallic nucleophiles has recently become an attractive alternative to conventional stoichiometric reagents in the stereoselective synthesis. Herein, we have developed an efficient and economical method to synthesize enantiopure α-hydroxy allyl ketones via a copper hydride (CuH)-catalyzed hydroacylation of alkoxyallenes, a significant advancement given the scarcity of reports on such scaffolds in the literature. DFT calculations reveal that this reaction proceeds through the nucleophilic attack of a kinetically favourable Z-selective allyl-copper intermediate on acid anhydrides via a six-membered chair-like transition state, stabilized by strongly attractive non-covalent interactions that ultimately leads to high level of enantioselectivities using the simple BINAP ligand.
View Article and Find Full Text PDFChemistryOpen
January 2025
Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, Liaoning, China.
A silver-catalyzed decarboxylative coupling of oxamic acids with styrenes has been developed to produce E-cinnamamides. Oxamic acids act as efficient precursors for carbamoy radicals. Based on the mechanistic experiments and intermediate analysis, the proposed mechanism involves radical addition to styrenes, followed by oxidation and solvent participation, ultimately leading to the formation of cinnamamides which is different from the reported cases.
View Article and Find Full Text PDFChem Asian J
January 2025
Shanghai University, Materials Genome Institute, Nanchen Road 333, 200444, Shanghai, CHINA.
MXene, a two-dimensional nanomaterial, has metal conductivity, high electronegativity, functionalized with surface groups, which makes them has wide applications in catalysis and biosensing. However, studies on the principle of enhanced electro-chemiluminescence (ECL) by MXene composites and the improvement of their performance in catalyzing the ECL reaction are still in their infancy. In this study, gold nanoparticles (AuNPs) are obtained by mild reductive reduction and loaded in situ on the Ti3C2Tx MXene surface to form the composites (AuNPs@MXene).
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
University of Amsterdam Faculty of Science: Universiteit van Amsterdam Faculteit der Natuurwetenschappen Wiskunde en Informatica, Van't Hoff Institute for Molecular Science, PO Box 94157, Science Park 904, 1090 GD, Amsterdam, NETHERLANDS, KINGDOM OF THE.
Cyclopropanes are valuable motifs in organic synthesis, widely featured in pharmaceuticals and functional materials. Herein, we report an efficient electrochemical methodology for the cyclopropanation of alkenes, leveraging a nickel-catalyzed process in continuous-flow. The developed protocol demonstrates broad substrate scope, accommodating both electron-rich and electron-poor alkenes with high functional group tolerance.
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