Schiff base Cu(I) catalyst for aerobic oxidation of primary alcohols

Molecular Catalysis - Tập 468 - Trang 75-79 - 2019
Emi Lagerspets1, Kalle Lagerblom1, Eeva Heliövaara1, Otto‐Matti Hiltunen1, Karina Moslova1, Martin Nieger1, Timo Repo1
1Department of Chemistry, University of Helsinki, P.O. Box 55, 00014 Helsinki, Finland

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Hudlicky, 1990

Tojo, 2006

Tojo, 2007

Caron, 2006, Large-scale oxidations in the pharmaceutical industry large, Chem. Rev., 106, 2943, 10.1021/cr040679f

Constable, 2007, Key green chemistry research areas—a perspective from pharmaceutical manufacturers, Green Chem., 9, 411, 10.1039/B703488C

Steinhoff, 2002, Mechanistic study of alcohol oxidation by the Pd(OAc)(2)/O- 2/DMSO catalyst system and implications for the development of improved aerobic oxidation catalysts, J. Am. Chem. Soc., 124, 766, 10.1021/ja016806w

Liu, 2017, A novel modified MIL-101-NH2ligand for CuI-catalyzed and air promoted oxidation of secondary alcohols, RSC Adv., 7, 22353, 10.1039/C7RA00296C

Jlassi, 2017, Arylhydrazone Cd(II) and Cu(II) complexes as catalysts for secondary alcohol oxidation, Polyhedron, 129, 182, 10.1016/j.poly.2017.03.020

Lepp, 1981, Copper, 111

Kesler, 2008, Earth’s copper resources estimated from tectonic diffusion of porphyry copper deposits, Geology., 36, 255, 10.1130/G24317A.1

Hemsworth, 2013, The Copper Active Site of CBM33 Polysaccharide Oxygenases, J. Am. Chem. Soc., 135, 6069, 10.1021/ja402106e

Festa, 2011, Copper: an essential metal in biology, Curr. Biol., 21, R877, 10.1016/j.cub.2011.09.040

Conry, 2006, copper: inorganic & coordination chemistry based in part on the article copper: inorganic & coordination chemistry by rebecca R. conry & kenneth D. karlin which appeared in the encyclopedia of inorganic chemistry

Whittaker, 1988, The active site of galactose oxidase, J. Biol. Chem., 263, 6074, 10.1016/S0021-9258(18)68751-4

Figiel, 2009, Aerobic oxidation of benzylic alcohols in water by 2,2,6,6- tetramethylpiperidine-1-oxyl(TEMPO)/Copper(II) 2-N-Arylpyrrolecarbaldimino complexes, Adv. Synth. Catal., 351, 2625, 10.1002/adsc.200900478

Figiel, 2007, TEMPO-copper(II) diimine-catalysed oxidation of benzylic alcohols in aqueous media, Adv. Synth. Catal., 349, 1173, 10.1002/adsc.200600505

Ahmad, 2009, Aerobic oxidation of benzylic alcohols with bis(3,5-di-tert-butylsalicylaldimine)copper(II) complexes, Appl. Catal. A Gen., 371, 17, 10.1016/j.apcata.2009.09.011

Zultanski, 2016, Practical synthesis of amides via Copper/ABNO-Catalyzed aerobic oxidative coupling of alcohols and amines, J. Am. Chem. Soc., 138, 6416, 10.1021/jacs.6b03931

Hoover, 2013, Mechanism of copper(I)/TEMPO-catalyzed aerobic alcohol oxidation, J. Am. Chem. Soc., 135, 2357, 10.1021/ja3117203

Steves, 2013, Copper(I)/ABNO-catalyzed aerobic alcohol oxidation: alleviating steric and electronic constraints of Cu/TEMPO catalyst systems, J. Am. Chem. Soc., 135, 15742, 10.1021/ja409241h

Gamez, 2003, Copper(II)-catalysed aerobic oxidation of primary alcohols to aldehydes, Chem. Commun. (Camb.), 2414, 10.1039/b308668b

Hoover, 2013, Copper/TEMPO-catalyzed aerobic alcohol oxidation: mechanistic assessment of different catalyst systems, ACS Catal., 3, 2599, 10.1021/cs400689a

del Mar Conejo, 2018, Synthesis, structure and properties of nickel and copper complexes containing N,O-hydrazone Schiff base ligand, Inorganica Chim. Acta, 470, 113, 10.1016/j.ica.2017.04.064

Czepa, 2018, Simple schiff-base Cu(II) complexes as efficient catalysts for benzyl alcohol oxidation, ChemistrySelect., 3, 9504, 10.1002/slct.201801550

Czepa, 2018, Simple schiff-base Cu(II) complexes as efficient catalysts for benzyl alcohol oxidation, ChemistrySelect., 3, 9504, 10.1002/slct.201801550

Al-Saeedi, 2018, Catalytic Oxidation of Benzyl Alcohol Using Nanosized Cu/Ni Schiff-Base Complexes and Their Metal Oxide Nanoparticles, Catalysts., 8, 452, 10.3390/catal8100452

Iovel, 2005, Synthesis and hydrosilylation of furan and thiophene N- methylenefluoroanilines in the presence of Pd(I) complex, Chem. Heterocycl., 41, 1112, 10.1007/s10593-005-0288-z

Sheldrick, 2008, A short history of SHELX, Acta Crystallogr. Sect. A Found. Crystallogr., 64, 112, 10.1107/S0108767307043930

Sheldrick, 2015, Crystal structure refinement with SHELXL, Acta Crystallogr. Sect. C Struct. Chem., 71, 3, 10.1107/S2053229614024218

Spek, 2009, Structure validation in chemical crystallography, Acta Crystallogr. Sect. D Biol. Crystallogr., 65, 148, 10.1107/S090744490804362X

Spek, 2015, PLATON SQUEEZE: a tool for the calculation of the disordered solvent contribution to the calculated structure factors, Acta Crystallogr. Sect. C Struct. Chem., 71, 9, 10.1107/S2053229614024929

Hörmannsdorfer, 2016, Synthesis and characterization of Cu(II)-halide 1-methylimidazole complexes, Zeitschrift Fur Naturforsch. - Sect. B J. Chem. Sci., 71, 105, 10.1515/znb-2015-0139

Mohamadou, 1998, Substituent Effects on the Redox Properties of some Bis(N-Arylpyrrole-2-carboxaldiminato)-copper(II) Complexes†, J. Chem. Res., 140, 10.1039/a708656c

Addison, 1978, Remote substituent effects in Pyrrole-2-carboxaldiminate complexes of copper(II), Inorg. Chem., 17, 2161, 10.1021/ic50186a026

Conry, 2006, Copper: inorganic & coordination ChemistryBased in part on the article copper: inorganic & coordination chemistry by rebecca R. conry & kenneth D. karlin which appeared in the encyclopedia of inorganic chemistry

Lagerblom, 2017, Practical Aerobic Oxidation of Alcohols: Ligand Enhanced TEMPO/Mn(NO3)2 Catalyst System, ChemCatChem., 10.1002/cctc.201700710

Hoover, 2013, Mechanism of copper (I)/ TEMPO-Catalyzed aerobic alcohol oxidation mechanism of copper (I)/ TEMPO-Catalyzed aerobic alcohol oxidation, J. Am. Chem. Soc., 135, 2357, 10.1021/ja3117203

Hoover, 2012, Copper(I)/TEMPO-catalyzed aerobic oxidation of primary alcohols to aldehydes with ambient air, Nat. Protoc., 7, 1161, 10.1038/nprot.2012.057