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An effective dual copper-and sulfide-catalytic system for the epoxidation of aldehydes with phenyldiazomethane

AutorPereira, A.; Martin, C.; Maya, Celia ; Belderrain, Tomás R.; Pérez, Pedro J.
Fecha de publicación2013
EditorJohn Wiley & Sons
CitaciónAdvanced Synthesis and Catalysis 355: 2942- 2951 (2013)
ResumenEpoxides have been obtained from alde-hydes and phenyldiazomethane using catalytic amounts of both the copper homoscorpionate com-plexes Tp xCuL (Tpx = homoscorpionate ligand; L = acetonitrile or tetrahydrofuran, THF) and dimethyl sulfide (SMe2) in high yields and diasteroselectivities, and with activities higher (TOF = 46 h-1) than those already known with rhodium-or copper-based cata-lysts. Among the copper(I) homoscorpionate com-plexes tested, TpBr3Cu(NCCH 3) showed the highest catalytic activity under mild conditions. The catalytic activity is controlled by electronic effects induced by the Tp x ligand as well as by the stability of the TpxCu(SR 2) adducts. Indeed, in the case of TpMs as ligand, the TpMsCu(THT) (THT = tetrahydrothio-phene) and Tp MsCu(SMe2) species could be isolated as very stable crystalline solids, the molecular struc-ture of the former being confirmed by single-crystal X-ray diffraction analysis. The in situ generation of PhCHN 2 from benzaldehyde tosylhydrazone sodium salt at 60 °C in methyl tert-butyl ether as solvent and TpMsCu(THF) as the catalyst also showed high cata-lytic activities, improving those already reported with copper-based catalysts. © 2013 Wiley-VCH Verlag GmbH&Co. KGaA, Weinheim.
Identificadoresdoi: 10.1002/adsc.201300606
issn: 1615-4150
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