Aerobic benzyl alcohol oxidation by copper(I) (2,2′-bipyridine)-based catalysts

被引:1
作者
Oberhauser, Werner [1 ]
Manca, Gabriele [1 ]
机构
[1] Ist Chim Composti Organometall CNR ICCOM, Via Madonna Piano 10, I-50019 Sesto Fiorentino, Italy
关键词
Copper (I); 2; 2' -Bipyridine ligands; Aerobic oxidation; Benzyl alcohol; NMR spectroscopy; COMPLEXES; SYSTEM; MECHANISM; ALDEHYDES; EFFICIENT; GREEN;
D O I
10.1016/j.ica.2024.121977
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
"In situ" prepared cationic Cu(I) complexes bearing 2,2'-bipyridine ligands and trifluoromethylsulfonate (triflate) have been used to catalyze the aerobic oxidation of benzyl alcohol to benzaldehyde in acetonitrile in the presence of (2,2,6,6-tetramethylpiperidin-1-yl) oxyl (TEMPO). A combination of catalytic reactions, operando 1H NMR spectroscopic studies and the analysis of the molecular structure of the Cu(I) precatalysts in acetonitrile by means of DFT calculations shed light on the notable influence of counter -anion ligand interactions on the observed catalytic activity.
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页数:8
相关论文
共 39 条
[1]   METHYL TRANSFER IN THE REACTION OF IRME3(PME2PH)3 WITH CU(NCME)4+ [J].
ALVAREZ, D ;
CAULTON, KG .
POLYHEDRON, 1988, 7 (14) :1285-1287
[2]   Quantum calculation of molecular energies and energy gradients in solution by a conductor solvent model [J].
Barone, V ;
Cossi, M .
JOURNAL OF PHYSICAL CHEMISTRY A, 1998, 102 (11) :1995-2001
[3]   Cu(bipy)2+/TEMPO-Catalyzed Oxidation of Alcohols: Radical or Nonradical Mechanism? [J].
Belanzoni, Paola ;
Michel, Carine ;
Baerends, Evert Jan .
INORGANIC CHEMISTRY, 2011, 50 (23) :11896-11904
[4]   Mechanistic Insight into the Alcohol Oxidation Mediated by an Efficient Green [CuBr2(2,2′-bipy)]-TEMPO Catalyst by Density Functional Method [J].
Cheng, Lin ;
Wang, Jinping ;
Wang, Meiyan ;
Wu, Zhijian .
INORGANIC CHEMISTRY, 2010, 49 (20) :9392-9399
[5]   Cu(II)-nitroxyl radicals as catalytic galactose oxidase mimics [J].
Dijksman, A ;
Arends, IWCE ;
Sheldon, RA .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (18) :3232-3237
[6]   Efficient and selective aerobic oxidation of alcohols into aldehydes and ketones using ruthenium/TEMPO as the catalytic system [J].
Dijksman, A ;
Marino-González, A ;
Payeras, AMI ;
Arends, IWCE ;
Sheldon, RA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (28) :6826-6833
[7]   RELATIVISTIC AND CORRELATION-EFFECTS FOR ELEMENT 105 (HAHNIUM, HA) - A COMPARATIVE-STUDY OF M AND MO (M = NB, TA, HA) USING ENERGY-ADJUSTED ABINITIO PSEUDOPOTENTIALS [J].
DOLG, M ;
STOLL, H ;
PREUSS, H ;
PITZER, RM .
JOURNAL OF PHYSICAL CHEMISTRY, 1993, 97 (22) :5852-5859
[8]  
Frisch M.J., 2013, GAUSSIAN 09
[9]   A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu [J].
Grimme, Stefan ;
Antony, Jens ;
Ehrlich, Stephan ;
Krieg, Helge .
JOURNAL OF CHEMICAL PHYSICS, 2010, 132 (15)
[10]   Copper/TEMPO-Catalyzed Aerobic Alcohol Oxidation: Mechanistic Assessment of Different Catalyst Systems [J].
Hoover, Jessica M. ;
Ryland, Bradford L. ;
Stahl, Shannon S. .
ACS CATALYSIS, 2013, 3 (11) :2599-2605