Efficient ligand-free palladium catalyzed Mizoroki-Heck reaction allowed the formation of trisubstituted α-trifluoromethylacrylates. The reaction showed good chemical tolerance and furnished moderate to excellent yields of reaction. Silver salt additive proved to be essential for the reaction. The reaction has been then applied to the formation of 3-trifluoromethyl coumarins and analogues of therapeutic agents.
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http://dx.doi.org/10.1021/acs.joc.8b03085 | DOI Listing |
Chem Commun (Camb)
January 2025
Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow, Uttar Pradesh 226031, India.
Biaryl motifs are essential structural features in several drugs and functional molecules. Cyclic diaryliodonium has been scarcely explored as a bifunctional agent compared to ring opening and annulation reactions. Herein, a three-component cascade approach is developed to synthesize bifunctionalized biaryls employing cyclic diaryliodoniums as a biarylating agent.
View Article and Find Full Text PDFRSC Med Chem
October 2024
Research Center on Fundamental and Applied Heterochemistry, Faculty of Chemistry and Chemical Engineering, Babeş-Bolyai University 11 Arany Janos str RO-400028 Cluj-Napoca Romania +40 264 593833.
New -substituted AB-type phenothiazinyl porphyrins and ferrocenylvinyl phenothiazinyl porphyrin were synthesised by Suzuki-Miyaura and Mizoroki-Heck cross-coupling reactions, respectively. The free porphyrins were further used in the synthesis of new indium(iii) or zinc(ii) porphyrin complexes. All porphyrins exhibit red fluorescence emission in solution, a property that remains unimpaired following internalisation in ovarian A2780 cancer cells, as evidenced by fluorescence microscopy images.
View Article and Find Full Text PDFFront Chem
October 2024
Department of Chemistry, Guru Ghasidas Vishwavidyalaya, Bilaspur, India.
We report the fabrication of a novel spinel-type Pd₀.₁Cu₀.₉Co₂O₄ nano-flake material designed for Mizoroki-Heck and Suzuki coupling-cum-transesterification reactions.
View Article and Find Full Text PDFTurk J Chem
January 2024
Department of Applied Chemistry and Life Science, Toyohashi University of Technology, Toyohashi, Aichi, Japan.
Cinchona alkaloid-derived sulfonamides and ester dimers containing chiral hyperbranched polymers have been successfully synthesized and applied as catalysts in asymmetric reactions. Several hyperbranched polymers derived from cinchona alkaloids, incorporating sulfonamides and esters, were synthesized through Mizoroki-Heck coupling polymerization. These polymers were subsequently applied in enantioselective Michael addition reactions.
View Article and Find Full Text PDFOrg Lett
September 2024
Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie-Curie, Ottawa, Ontario K1N 6N5, Canada.
We report a palladium-catalyzed synthesis of α-vinyl boronates via a regioselective Mizoroki-Heck reaction between aryl triflates and vinyl boronates. This selectivity is achieved by the use of a 1,5-diaza-3,7-diphosphacyclooctane (PN) ligand, which results in minimal formation of the more commonly observed (linear) β-product. The choice of base, solvent, and presence of water are shown to be critical for controlling this outcome, with organic bases, nonpolar solvents, and anhydrous conditions favoring the Heck product and suppressing the competitive Suzuki-Miyaura coupling product.
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