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Synthesis of Fused Tetracyclic Compounds via Oxidative Annulation: Access to Copper-Catalyzed Indolo[1,2-]quinolines and to Ruthenium-Catalyzed Isoquinolin-1[2]-ones.
J Org Chem
May 2023
Univ Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) - UMR 6226, F-35000 Rennes, France.
A facile double oxidative annulation of (en-3-yn-1-yl)phenylbenzamides was developed allowing us to synthetize fused tetracyclic compounds. Under copper catalysis, the reaction proceeds with high efficiency and leads to new indolo[1,2-]quinolines via a decarbonylative double oxidative annulation. On the other hand, under ruthenium catalysis, new isoquinolin-1[2]-ones were obtained via a double oxidative annulation.
View Article and Find Full Text PDFRevised Mechanism for a Ruthenium-Catalyzed Coupling of Aldehyde and Terminal Alkyne.
ACS Omega
March 2018
Department of Chemistry and FQRNT Centre for Green Chemistry and Catalysis, McGill University, Montréal, Quebec, Canada H3A 0B8.
Ruthenium catalysts have been found to be of great use for many kinds of reactions. Understanding the details of the catalytic cycle allows to not only rationalize experimental results but also to improve upon reactions. Herein, we present a detailed computational study of a ruthenium-catalyzed coupling between a terminal alkyne and an aldehyde.
View Article and Find Full Text PDFRuthenium-catalyzed decarbonylative addition reaction of anhydrides with alkynes: a facile synthesis of isocoumarins and α-pyrones.
Chem Commun (Camb)
June 2015
Medicinal Chemistry Division, CSIR-North East Institute of Science and Technology, Jorhat 785006, India.
A novel ruthenium catalyzed straightforward and efficient synthesis of isocoumarin and α-pyrone derivatives has been accomplished by the decarbonylative addition reaction of anhydrides with alkynes under thermal conditions.
View Article and Find Full Text PDFRemarkable improvement achieved by imidazole derivatives in ruthenium-catalyzed hydroesterification of alkenes using formates.
Org Lett
September 2012
School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Shizuoka 422-8526, Japan.
Imidazole derivatives are revealed to be effective ligands in the Ru-catalyzed hydroesterification of alkenes using formates, affording one-carbon-elongated esters in high yields. Further, intramolecular hydroesterification was successfully performed to give lactones for the first time. Imidazole derivatives can contribute to promote the reaction as well as to suppress the undesired decarbonylation of formate.
View Article and Find Full Text PDFRu-catalyzed decarbonylative addition of aliphatic aldehydes to terminal alkynes.
Org Lett
July 2010
Department of Chemistry, McGill University, 801 Sherbrooke St. West, Montreal, Quebec H3A 2K6, Canada.
A novel method for the formation of isolated C=C bonds was developed via a ruthenium-catalyzed decarbonylative addition of aliphatic aldehydes and alkynes. An unprecedented complete switch of chemoselectivity from aromatic aldehydes to aliphatic aldehydes was observed simply by using tri(2,4,6-trismethoxyphenyl)phosphine as ligand. A synthesis by this method of an insect sex pheromone was demonstrated.
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