BIOMAT Database Logo BIOMAT Database Logo

Ce(OTf)₃-catalyzed [3 + 2] cycloaddition of azides with nitroolefins: regioselective synthesis of 1,5-disubstituted 1,2,3-triazoles. 2014

Ying-Chun Wang, and Yu-Yang Xie, and Hong-En Qu, and Heng-Shan Wang, and Ying-Ming Pan, and Fu-Ping Huang
Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), School of Chemistry & Chemical Engineering of Guangxi Normal University , Guilin 541004, People's Republic of China.

The first example of rare earth metal-catalyzed [3 + 2] cycloaddition of organic azides with nitroolefins and subsequent elimination reaction is described. In the presence of a catalytic amount of Ce(OTf)3, both benzyl and phenyl azides react with a broad range of aryl nitroolefins containing a range of functionalities selectively producing 1,5-disubstituted 1,2,3-triazoles in good to excellent yields.

UI MeSH Term Description Entries
D008698 Mesylates Organic salts or esters of methanesulfonic acid. Mesilate,Methanesulfonates,Mesilates,Mesylate,Methylenesulfonates
D009574 Nitro Compounds Compounds having the nitro group, -NO2, attached to carbon. When attached to nitrogen they are nitramines and attached to oxygen they are NITRATES. Nitrated Compounds
D002384 Catalysis The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction. Catalyses
D000475 Alkenes Unsaturated hydrocarbons of the type Cn-H2n, indicated by the suffix -ene. (Grant & Hackh's Chemical Dictionary, 5th ed, p408) Alkene,Olefin,Olefins,Pentene,Pentenes
D001386 Azides Organic or inorganic compounds that contain the -N3 group. Azide
D001593 Benzyl Compounds Benzene derivatives that contain a benzyl group with the general formula Phenyl-CH2-R. Compounds, Benzyl
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D014230 Triazoles Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3. Triazole
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D061565 Cycloaddition Reaction Synthetic organic reactions that use reactions between unsaturated molecules to form cyclical products. Cycloaddition,Cycloaddition Reaction Techniques,Diels-Alder Reaction,Cycloaddition Reaction Technique,Cycloaddition Reactions,Diels Alder Reaction,Reaction Technique, Cycloaddition,Reaction Techniques, Cycloaddition,Reaction, Cycloaddition,Reaction, Diels-Alder,Reactions, Cycloaddition,Technique, Cycloaddition Reaction,Techniques, Cycloaddition Reaction

Related Publications

Ying-Chun Wang, and Yu-Yang Xie, and Hong-En Qu, and Heng-Shan Wang, and Ying-Ming Pan, and Fu-Ping Huang
Copper-catalyzed decarboxylative regioselective synthesis of 1,5-disubstituted 1,2,3-triazoles.
March 2018, Chemical communications (Cambridge, England),
Ying-Chun Wang, and Yu-Yang Xie, and Hong-En Qu, and Heng-Shan Wang, and Ying-Ming Pan, and Fu-Ping Huang
Ln[N(SiMe3)2]3-catalyzed cycloaddition of terminal alkynes to azides leading to 1,5-disubstituted 1,2,3-triazoles: new mechanistic features.
June 2013, Chemical communications (Cambridge, England),
Ying-Chun Wang, and Yu-Yang Xie, and Hong-En Qu, and Heng-Shan Wang, and Ying-Ming Pan, and Fu-Ping Huang
Preparation of 1,5-Disubstituted 1,2,3-Triazoles via Ruthenium-catalyzed Azide Alkyne Cycloaddition.
January 2013, Organic syntheses; an annual publication of satisfactory methods for the preparation of organic chemicals,
Ying-Chun Wang, and Yu-Yang Xie, and Hong-En Qu, and Heng-Shan Wang, and Ying-Ming Pan, and Fu-Ping Huang
An organocatalytic azide-aldehyde [3+2] cycloaddition: high-yielding regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles.
September 2014, Angewandte Chemie (International ed. in English),
Ying-Chun Wang, and Yu-Yang Xie, and Hong-En Qu, and Heng-Shan Wang, and Ying-Ming Pan, and Fu-Ping Huang
Copper-catalyzed [3 + 2] cycloaddition/oxidation reactions between nitro-olefins and organic azides: highly regioselective synthesis of NO2-substituted 1,2,3-triazoles.
March 2015, Organic letters,
Ying-Chun Wang, and Yu-Yang Xie, and Hong-En Qu, and Heng-Shan Wang, and Ying-Ming Pan, and Fu-Ping Huang
An Organocatalytic Regiospecific Synthesis of 1,5-Disubstituted 4-Thio-1,2,3-triazoles and 1,5-Disubstituted 1,2,3-Triazoles.
November 2015, Chemistry (Weinheim an der Bergstrasse, Germany),
Ying-Chun Wang, and Yu-Yang Xie, and Hong-En Qu, and Heng-Shan Wang, and Ying-Ming Pan, and Fu-Ping Huang
[3 + 2] Cycloaddition of acetylenes with azides to give 1,4-disubstituted 1,2,3-triazoles in a modular flow reactor.
May 2007, Organic & biomolecular chemistry,
Ying-Chun Wang, and Yu-Yang Xie, and Hong-En Qu, and Heng-Shan Wang, and Ying-Ming Pan, and Fu-Ping Huang
Metal-Free Synthesis of 1,5-Disubstituted 1,2,3-Triazoles.
December 2021, The Journal of organic chemistry,
Ying-Chun Wang, and Yu-Yang Xie, and Hong-En Qu, and Heng-Shan Wang, and Ying-Ming Pan, and Fu-Ping Huang
[3 + 2] Cycloaddition of Isocyanides with Aryl Diazonium Salts: Catalyst-Dependent Regioselective Synthesis of 1,3- and 1,5-Disubstituted 1,2,4-Triazoles.
November 2018, Organic letters,
Ying-Chun Wang, and Yu-Yang Xie, and Hong-En Qu, and Heng-Shan Wang, and Ying-Ming Pan, and Fu-Ping Huang
Copper-catalyzed azide-alkyne cycloaddition: regioselective synthesis of 1,4,5-trisubstituted 1,2,3-triazoles.
January 2010, Angewandte Chemie (International ed. in English),
Copied contents to your clipboard!