Department of Organic Chemistry, University of Madras, Guindy Campus, Tamilnadu, Chennai 600025, India.
Published: December 2024
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Article Abstract
A simple and efficient Ru(II)-catalyzed olefination of 3-(arylbenzylidene)indolin-2-ones with alkenes is described. This is an atom and step-economical strategy with a wide substrate scope, good functional group tolerance, and suitability for gram scale synthesis. A plausible mechanism is also proposed for this synthetic transformation involving the formation of a 5-membered ruthenacycle and insertion of the alkene followed by β-hydride elimination to deliver the desired product.
A simple and efficient Ru(II)-catalyzed olefination of 3-(arylbenzylidene)indolin-2-ones with alkenes is described. This is an atom and step-economical strategy with a wide substrate scope, good functional group tolerance, and suitability for gram scale synthesis. A plausible mechanism is also proposed for this synthetic transformation involving the formation of a 5-membered ruthenacycle and insertion of the alkene followed by β-hydride elimination to deliver the desired product.
The C-C bond formation reactions are important in organic synthesis. Heck reaction is known to arylate the terminal carbon of olefins; however, direct alkylation of the terminal carbon of olefin is limited. Herein, we report a novel ruthenium-catalyzed selective cross-coupling reaction of styrene and α-diazoesters to form a new C-C bond over cyclopropanation via the C-H insertion process for the first time.
An asymmetric synthesis of the tetrahydronaphthyridine scaffold of TAK-828F as a RORγt inverse agonist has been developed. The synthesis features a newly discovered atom-economical protocol for Heck-type vinylation of chloropyridine using ethylene gas, an unprecedented formation of dihydronaphthyridine directly from 2-vinyl-3-acylpyridine mediated by ammonia, and a ruthenium-catalyzed enantioselective transfer hydrogenation as key steps. This represents the first example of the enantioselective synthesis of a 5,6,7,8-tetrahydro-1,6-naphthyridine compound.
A novel reaction mode and efficient ruthenium-catalyzed Matsuda-Heck-type arylation of -quinone methides (-QMs) with aryl diazonium salts has been developed for the synthesis of symmetrical or unsymmetrical δ,δ'-diaryl quinone methides (fuchsones). Aryl groups are introduced at the δ-position of -QMs via tandem olefin insertion reaction/β-H elimination processes. This reaction features advantages such as mild and green conditions, broad reactant scope, and high yields.
Laboratorio de Compuestos Organometálicos y Catálisis (Unidad Asociada al CSIC), Departamento de Química Orgánica e Inorgánica (IUQOEM), Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Oviedo, Oviedo, Spain.
The self-assembly of styrene-type olefins into the corresponding stilbenes was conveniently performed in the () mixture 1/2 under air and in the absence of hazardous organic co-solvents using a one-pot chemo-biocatalytic route. Here, an enzymatic decarboxylation of -hydroxycinnamic acids sequentially followed by a ruthenium-catalyzed metathesis of olefins has been investigated in . Moreover, and to extend the design of chemoenzymatic processes in , we also coupled the aforementioned enzymatic decarboxylation reaction to now concomitant Pd-catalyzed Heck-type C-C coupling to produce biaryl derivatives under environmentally friendly reaction conditions.
