76960-00-4Relevant articles and documents
Preparation of aromatic γ-hydroxyketones by means of Heck coupling of aryl halides and 2,3-dihydrofuran, catalyzed by a palladium(ii) glycine complex under microwave irradiation
Jiménez-Cruz, Juan C.,Guzmán-Mejía, Ramón,Juaristi, Eusebio,Sánchez-Antonio, Omar,García-Revilla, Marco A.,González-Campos, J. Betzabe,Avi?a-Verduzco, Judit
, p. 13382 - 13392 (2020/08/28)
A series of aromatic γ-hydroxyketones were prepared by means of Heck coupling reaction of aryl halides and 2,3-dihydrofuran, catalyzed by PdCl2·Gly2 and under microwave irradiation. This synthetic transformation involves the formation of an aryl-dihydrofuranoic intermediate, followed by an unusual opening of the heterocycle promoted by a water molecule and the formation of the ketone carbonyl function through keto-enol tautomerism. This journal is
A synergistic LUMO lowering strategy using Lewis acid catalysis in water to enable photoredox catalytic, functionalizing C-C cross-coupling of styrenes
Speckmeier, Elisabeth,Fuchs, Patrick J. W.,Zeitler, Kirsten
, p. 7096 - 7103 (2018/09/25)
Easily available α-carbonyl acetates serve as convenient alkyl radical source for an efficient, photocatalytic cross-coupling with a great variety of styrenes. Activation of electronically different α-acetylated acetophenone derivatives could be effected via LUMO lowering catalysis using a superior, synergistic combination of water and (water-compatible) Lewis acids. Deliberate application of fac-Ir(ppy)3 as photocatalyst to enforce an oxidative quenching cycle is crucial to the success of this (umpolung type) transformation. Mechanistic particulars of this dual catalytic coupling reaction have been studied in detail using both Stern-Volmer and cyclic voltammetry experiments. As demonstrated in more than 30 examples, our water-assisted LA/photoredox catalytic activation strategy allows for excess-free, equimolar radical cross-coupling and subsequent formal Markovnikov hydroxylation to versatile 1,4-difunctionalized products in good to excellent yields.
TRAPPING THE INTERMEDIATE INVOLVED IN THE INTRAMOLECULAR CYCLISATION OF CYCLOPROPYL KETONES. A CONVENIENT PREPARATION OF OPEN-CHAIN γ-HYDROXY KETONES.
Murphy, William S.,Wattanasin, Sompong
, p. 3517 - 3520 (2007/10/02)
The concerted mechanism for the stannic chloride catalysed cyclisation of aryl cyclopropyl ketones is disproved by trapping the intermediate.The reaction provides a facile route to γ-hydroxyketones.