A copper complex bearing a TEMPO moiety as catalyst for the aerobic oxidation of primary alcohols
作者： Zhengliang Lu , José Sánchez Costa , Olivier Roubeau , Ilpo Mutikainen , Urho Turpeinen
DOI: 10.1039/B802109K
关键词:
摘要: A new bifunctional, triazine-based ligand has been designed with the aim to generate a copper(II) complex holding TEMPO (2,2,6,6-tetramethylpiperidinyloxy) moiety. The coordination compound obtained from 4-(2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)ethoxy)-6-(4-amino-2,2,6,6-tetramethylpiperidine-1-oxyl)-N,N-diphenyl-1,3,5-triazin-2-amine (pypzt-1) and bromide (i.e. 8) is capable of catalysing selective, aerobic oxidation benzyl alcohol 84% benzaldehyde in 24 h. This “galactose oxidase activity” copper/TEMPO observed as well for conversion non-activated alkyl octan-1-ol octanal yield 29% after same reaction time. single-crystal X-ray structure 8 shows that its crystal lattice contains [CuIBr2]− anions which appear be stabilised by means both anion–π hydrogen bonding interactions. In addition, solid state exhibits (lone-pair)–π interactions between nitrogen atom an acetonitrile molecule triazine ring. magnetic properties have investigated EPR susceptibility measurements.
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Sandra S. Eaton, Gareth R. Eaton, Interaction of spin labels with transition metals: Part 2 Coordination Chemistry Reviews. ,vol. 83, pp. 29- 72 ,(1988) , 10.1016/0010-8545(88)80018-3
S. S. Stahl, Palladium-Catalyzed Oxidation of Organic Chemicals with O2 Science. ,vol. 309, pp. 1824- 1826 ,(2005) , 10.1126/SCIENCE.1114666
Imtiaz A. Ansari, Rene Gree, TEMPO-Catalyzed Aerobic Oxidation of Alcohols to Aldehydes and Ketones in Ionic Liquid [bmim][PF6] Organic Letters. ,vol. 4, pp. 1507- 1509 ,(2002) , 10.1021/OL025721C
Bodo Betzemeier, Marco Cavazzini, Silvio Quici, Paul Knochel, Copper-catalyzed aerobic oxidation of alcohols under fluorous biphasic conditions Tetrahedron Letters. ,vol. 41, pp. 4343- 4346 ,(2000) , 10.1016/S0040-4039(00)00620-1
Yuji Mikata, Tomomi Fujimoto, Yuko Sugai, Shigenobu Yano, Control of Intramolecular Ether‐Oxygen Coordination in the Crystal Structure of Copper(II) Complexes With Dipicolylamine‐Based Ligands European Journal of Inorganic Chemistry. ,vol. 2007, pp. 1143- 1149 ,(2007) , 10.1002/EJIC.200600801
Carsten Bolm, Angelika S. Magnus, Jens P. Hildebrand, Catalytic synthesis of aldehydes and ketones under mild conditions using TEMPO/Oxone Organic Letters. ,vol. 2, pp. 1173- 1175 ,(2000) , 10.1021/OL005792G
Jorge Salinas Uber, Yorick Vogels, Dave van den Helder, Ilpo Mutikainen, Urho Turpeinen, Wen Tian Fu, Olivier Roubeau, Patrick Gamez, Jan Reedijk, Pyrazole-based ligands for the [copper-TEMPO]-mediated oxidation of benzyl alcohol to benzaldehyde and structures of the cu coordination compounds European Journal of Inorganic Chemistry. ,vol. 2007, pp. 4197- 4206 ,(2007) , 10.1002/EJIC.200700424
Paweł J. Figiel, Markku Leskelä, Timo Repo, TEMPO-Copper(II) Diimine-Catalysed Oxidation of Benzylic Alcohols in Aqueous Media Advanced Synthesis & Catalysis. ,vol. 349, pp. 1173- 1179 ,(2007) , 10.1002/ADSC.200600505
David Geißlmeir, Walther G. Jary, Heinz Falk, The TEMPO /Copper Catalyzed Oxidation of Primary Alcohols to Aldehydes Using Oxygen as Stoichiometric Oxidant Monatshefte Fur Chemie. ,vol. 136, pp. 1591- 1599 ,(2005) , 10.1007/S00706-005-0349-0
Brandi L. Schottel, Helen T. Chifotides, Kim R. Dunbar, Anion-π interactions Chemical Society Reviews. ,vol. 37, pp. 68- 83 ,(2008) , 10.1039/B614208G