Vanadium catalyzed aerobic carbon-carbon cleavage

被引:63
作者
Amadio, Emanuele [1 ]
Di Lorenzo, Rosalia [1 ]
Zonta, Cristiano [1 ,2 ]
Licini, Giulia [1 ,2 ,3 ]
机构
[1] Univ Padua, Dipartimento Sci Chim, I-35131 Padua, Italy
[2] CIRCC, I-70126 Bari, Italy
[3] Univ Libre Bruxelles, Ecole Polytechn Bruxelles, Engn Mol NanoSyst, B-1050 Brussels, Belgium
关键词
Vanadium complexes; Vanadium catalyzed oxidations; Carbon-carbon oxidative 1,2-diol cleavage; Aerobic oxidative C-C bond cleavage; Lignin and lignin model oxidation; Carbohydrates aerobic and anaerobic oxidation; C-C BOND; OXIDATIVE CLEAVAGE; VICINAL DIOLS; VIC-DIOLS; ORGANIC-COMPOUNDS; MOLECULAR-OXYGEN; QUINQUEVALENT VANADIUM; DITERTIARY GLYCOLS; ELECTRON-TRANSFER; MILD CONDITIONS;
D O I
10.1016/j.ccr.2015.06.004
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
In recent years, the use of vanadium complexes as catalysts and air or oxygen as oxidants has emerged as a new method for the effective oxidative carbon-carbon bond cleavage in a series of substrates, including 1,2-diols and alpha-hydroxy ethers. In addition to the advantageous use as a synthetic tool, vanadium catalyzed aerobic C-C bond cleavage becomes even more appealing if applied to the degradation of lignocellulosic biomass and in particular in the oxidative depolymerization/degradation of lignin or cellulose. In this review, this chemistry, the most recent advances and the role played by homogeneous vanadium complexes are presented and discussed. (C) 2015 Elsevier B.V. All rights reserved.
引用
收藏
页码:147 / 162
页数:16
相关论文
共 92 条
[51]  
Malaprade L, 1928, CR HEBD ACAD SCI, V186, P382
[52]  
Malaprade L., 1928, Bulletin de la Societe Chimique de France, V43, P683
[53]   Aerobic oxidative cleavage of pinanediols by cobalt(II) acetylacetonate in the presence of 2-methylpropanal [J].
Mastrorilli, P ;
Suranna, GP ;
Nobile, CF ;
Farinola, G ;
Lopez, L .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2000, 156 (1-2) :279-281
[54]   Vanadium complexes immobilized on solid supports and their use as catalysts for oxidation and functionalization of alkanes and alkenes [J].
Maurya, Mannar R. ;
Kumar, Amit ;
Pessoa, J. Costa .
COORDINATION CHEMISTRY REVIEWS, 2011, 255 (19-20) :2315-2344
[55]   Oxidative cleavage of vicinal diols: IBX can do what Dess-Martin periodinane (DMP) can [J].
Moorthy, Jarugu Narasimha ;
Singhal, Nidhi ;
Senapati, Kalyan .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (05) :767-771
[56]   OXIDATIVE CLEAVAGE OF ALPHA-DIOLS, ALPHA-DIONES, ALPHA-HYDROXY-KETONES AND ALPHA-HYDROXY ACIDS AND ALPHA-KETO ACIDS WITH CALCIUM HYPOCHLORITE [CA(OC1)2] [J].
NWAUKWA, SO ;
KEEHN, PM .
TETRAHEDRON LETTERS, 1982, 23 (31) :3135-3138
[57]   CONVERSION OF VICINAL DIOLS INTO DICARBONYL-COMPOUNDS BY MANGANESE-DIOXIDE [J].
OHLOFF, G ;
GIERSCH, W .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1973, 12 (05) :401-402
[58]   BIOMIMETIC OXIDATION WITH MOLECULAR-OXYGEN - SELECTIVE CARBON CARBON BOND-CLEAVAGE OF 1,2-DIOLS BY MOLECULAR-OXYGEN AND DIHYDROPYRIDINE IN THE PRESENCE OF IRON PORPHYRIN CATALYSTS [J].
OKAMOTO, T ;
SASAKI, K ;
OKA, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (04) :1187-1196
[59]   CATALYSIS OF AEROBIC C-C BOND-CLEAVAGE OF 1,2-BIS(4-METHOXYPHENYL)ETHANE-1,2-DIOL BY MESO-TETRAPHENYLPORPHYRINATOIRON(III) - A MODEL SYSTEM FOR CYTOCHROME P-450SCC DEPENDENT GLYCOL CLEAVAGE [J].
OKAMOTO, T ;
SASAKI, K ;
SHIMADA, M ;
OKA, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (07) :381-383
[60]   In situ oxidative diol cleavage-Wittig processes [J].
Outram, HS ;
Raw, SA ;
Taylor, RJK .
TETRAHEDRON LETTERS, 2002, 43 (35) :6185-6187