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Novel metal-free Lewis acid catalysis by phosphonium salts through hypervalent interaction
Affiliation:1. Merck KGaA, PM-ATI, Frankfurter Str. 250, D-64293 Darmstadt, Germany;2. Universität Bielefeld, Anorganische Chemie, Universitätsstraße 25, 33615 Bielefeld, Germany;3. Heinrich-Heine-Universität Düsseldorf, Institut für Anorganische Chemie und Strukturchemie II, Universitätstrasse 1, 40225 Düsseldorf, Germany;4. Bergische Universität Wuppertal, Anorganische Chemie, Gauss Strasse 20, D-42097 Wuppertal, Germany;1. Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Via Moruzzi 13, 56124 Pisa, Italy;2. INSTM, UdR Pisa, Via Moruzzi 13, 56124 Pisa, Italy;1. A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., Moscow, 119991, Russian Federation;2. State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China;1. Institute of Inorganic Chemistry, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Straße 1, 53121 Bonn, Germany;2. Sant Longowal Institute of Engineering and Technology, Longowal 148106, Distt. Sangrur (Pb.), India;3. Department of Organic Chemistry, Faculty of Chemistry, University of Murcia, Campus de Espinardo, 30100 Murcia, Spain
Abstract:Phosphonium salts as a novel metal-free Lewis acid catalyst can be considered as organocatalysts. The introduction of a five-membered dioxaphosphacycle to the phosphonium salt is critical to its function as a Lewis acid catalyst for the Diels–Alder reaction. The key to the successful catalysis by the phosphonium salt is the utilization of hypervalent bonding as a strategic interaction for the generation of an active species.
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