Copper-catalyzed arylation of electron rich alkynes reveals stabilized trisubstituted vinyl cation equivalents that react with pendant arene nucleophiles to form all carbon tetrasubstituted alkenes. The new process streamlines the synthesis of important medicinally relevant molecules.
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http://dx.doi.org/10.1021/ja405972h | DOI Listing |
Acc Chem Res
December 2024
Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, China.
Org Lett
June 2021
Department of Chemistry, University of Texas at Austin, 100 East 24th Street, Austin, Texas 78712, United States.
A general system achieving three-component intermolecular carbofunctionalization of alkenes is presented, including carboetherification, carboesterification, carboarylation, and carboamination. The scope of the reaction is presented with respect to the carbon electrophile, the olefin, and the nucleophile. Furthermore, the synthesis of γ-lactams a carboamination reaction is demonstrated in a telescoped three-step protocol.
View Article and Find Full Text PDFOrg Lett
September 2015
MTA-ELTE "Lendület" Catalysis and Organic Synthesis Research Group, Institute of Chemistry, Eötvös University, Pázmány Péter stny. 1/a, H-1117 Budapest, Hungary.
A copper-catalyzed carboarylation-ring-closure strategy was used for the modular synthesis of oxazolines via the reaction of 1-aryl- and 1-alkylpropargylamides and diaryliodonium salts. The novel approach enables the efficient, modular synthesis of oxazoline derivatives bearing fully substituted exo double bonds.
View Article and Find Full Text PDFOrg Lett
November 2013
MTA-ELTE "Lendület" Catalysis and Organic Synthesis Research Group, Institute of Chemistry, Eötvös University , Pázmány Péter stny. 1/a, H-1117 Budapest, Hungary , Servier Research Institute of Medicinal Chemistry , Záhony utca 7, H-1031 Budapest, Hungary , and Research Centre for Natural Sciences, Hungarian Academy of Sciences , Pusztaszeri út 59-67, H-1025 Budapest, Hungary.
A new copper-catalyzed oxidative ring closure of ethynyl anilides with diaryliodonium salts was developed for the highly modular construction of benzoxazines bearing a fully substituted exo double bond. The oxidative transformation includes an unusual 6-exo-dig cyclization step with the formation of C-O and C-C bonds.
View Article and Find Full Text PDFJ Am Chem Soc
August 2013
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, United Kingdom, CB2 1EW.
Copper-catalyzed arylation of electron rich alkynes reveals stabilized trisubstituted vinyl cation equivalents that react with pendant arene nucleophiles to form all carbon tetrasubstituted alkenes. The new process streamlines the synthesis of important medicinally relevant molecules.
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