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Indoles from Alkynes and Aryl Azides: Scope and Theoretical Assessment of Ruthenium Porphyrin-Catalyzed Reactions.
Chemistry
December 2019
Istituto di Chimica dei Composti OrganoMetallici, ICCOM-CNR, Via Madonna del Piano 10, 50019, Sesto Fiorentino, Italy.
A symbiotic experimental/computational study analyzed the Ru(TPP)(NAr) -catalyzed one-pot formation of indoles from alkynes and aryl azides. Thirty different C -substituted indoles were synthesized and the best performance, in term of yields and regioselectivities, was observed when reacting ArC≡CH alkynes with 3,5-(EWG) C H N azides, whereas the reaction was less efficient when using electron-rich aryl azides. A DFT analysis describes the reaction mechanism in terms of the energy costs and orbital/electronic evolutions; the limited reactivity of electron-rich azides was also justified.
View Article and Find Full Text PDFArylruthenium(III) Porphyrin-Catalyzed C-H Oxidation and Epoxidation at Room Temperature and [Ru(Por)(O)(Ph)] Intermediate by Spectroscopic Analysis and Density Functional Theory Calculations.
J Am Chem Soc
June 2018
Department of Chemistry and State Key Laboratory of Synthetic Chemistry , The University of Hong Kong, Pokfulam Road , Hong Kong , China.
The development of highly active and selective metal catalysts for efficient oxidation of hydrocarbons and identification of the reactive intermediates in the oxidation catalysis are long-standing challenges. In the rapid hydrocarbon oxidation catalyzed by ruthenium(IV) and -(III) porphyrins, the putative Ru(V)-oxo intermediates remain elusive. Herein we report that arylruthenium(III) porphyrins are highly active catalysts for hydrocarbon oxidation.
View Article and Find Full Text PDFA theoretical study on the oxidation of alkenes to aldehydes catalyzed by ruthenium porphyrins using O as the sole oxidant.
Dalton Trans
April 2018
Department of Chemistry, the University of Hong Kong, Hong Kong, P. R. China.
Density functional theory (DFT) calculations were used to study the ruthenium porphyrin-catalyzed oxidation of styrene to generate an aldehyde. The results indicate that two reactive oxidants, dioxoruthenium and monooxoruthenium-superoxo porphyrins, participate in the catalytic oxidation. In the mechanism, the resultant monooxoruthenium porphyrin acts in the tandem epoxide isomerization (E-I) to selectively yield an aldehyde and generate a dioxoruthenium porphyrin, thereby triggering new oxidation reaction cycles.
View Article and Find Full Text PDFRuthenium-Porphyrin-Catalyzed [4 + 2] Cycloaddition of α,β-Unsaturated Imines and Aldehydes.
Org Lett
November 2015
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan.
A new efficient synthetic route to unsymmetrically substituted dihydropyridine scaffolds via dehydrative [4 + 2] cycloaddition of N-tosylated α,β-unsaturated imines with aldehydes has been developed. This transformation is enabled by (i) the remarkable catalytic ability of the cationic Ru(IV) porphyrin complex to activate both the imino and carbonyl groups and (ii) the hydrophobic nature of the porphyrin ligand, which helps realize robust Lewis acidity in the dehydrative cycloaddition.
View Article and Find Full Text PDFRuthenium-porphyrin-catalyzed diastereoselective intramolecular alkyl carbene insertion into C-H bonds of alkyl diazomethanes generated in situ from N-tosylhydrazones.
Angew Chem Int Ed Engl
December 2014
HKU Shenzhen Institute of Research and Innovation, Shenzhen (China); State Key Laboratory of Synthetic Chemistry and Department of Chemistry, The University of Hong Kong, Hong Kong (China).
With a ruthenium-porphyrin catalyst, alkyl diazomethanes generated in situ from N-tosylhydrazones efficiently underwent intramolecular C(sp(3))-H insertion of an alkyl carbene to give substituted tetrahydrofurans and pyrrolidines in up to 99% yield and with up to 99:1 cis selectivity. The reaction displays good tolerance of many functionalities, and the procedure is simple without the need for slow addition with a syringe pump. From a synthetic point of view, the C-H insertion of N-tosylhydrazones can be viewed as reductive coupling between a C=O bond and a C-H bond to form a new C-C bond, since N-tosylhydrazones can be readily prepared from carbonyl compounds.
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