Selective Iron-Catalyzed Oxidation of Benzylic and Allylic Alcohols

被引:54
作者
Join, Benoit [1 ]
Moeller, Konstanze [1 ]
Ziebart, Carolin [1 ]
Schroeder, Kristin [1 ]
Goerdes, Dirk [2 ]
Thurow, Kerstin [2 ]
Spannenberg, Anke [1 ]
Junge, Kathrin [1 ]
Beller, Matthias [1 ]
机构
[1] Univ Rostock, Leibniz Inst Katalyse eV, D-18059 Rostock, Germany
[2] Univ Rostock, Ctr Life Sci Automat CELISCA, D-18119 Rostock, Germany
关键词
alcohols; catalysis; hydrogen peroxide; iron; oxidation; ASYMMETRIC TRANSFER HYDROGENATION; SATURATED-HYDROCARBONS; SULFIDE OXIDATION; AEROBIC OXIDATION; EFFICIENT; PEROXIDE; EPOXIDATION; OLEFINS; HYDROSILYLATION; COMPLEXES;
D O I
10.1002/adsc.201100210
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A convenient and selective oxidation of alcohols with hydrogen peroxide to give aldehydes and ketones has been developed. Using in situ generated iron chloride complexes [Fe(L3)2Cln] [n=01, L3 =6-(N-phenylbenzimidazoyl)-2-pyridinecarboxylic acid], aldehydes and ketones were obtained in good yield and excellent selectivity after a short reaction time at room temperature.
引用
收藏
页码:3023 / 3030
页数:8
相关论文
共 79 条
[1]   Chemo- and Stereoselective Iron-Catalyzed Hydrosilylation of Ketones [J].
Addis, Daniele ;
Shaikh, Nadim ;
Zhou, Shaolin ;
Das, Shoubhik ;
Junge, Kathrin ;
Beller, Matthius .
CHEMISTRY-AN ASIAN JOURNAL, 2010, 5 (07) :1687-1691
[2]  
Adolfsson H., 2011, MODERN OXIDATION MET
[3]   Solvent free oxidation of primary alcohols and diols using thymine iron(III) catalyst [J].
Al-Hunaiti, Afnan ;
Niemi, Teemu ;
Sibaouih, Ahlam ;
Pihko, Petri ;
Leskela, Markku ;
Repo, Timo .
CHEMICAL COMMUNICATIONS, 2010, 46 (48) :9250-9252
[4]   An efficient biomimetic Fe-catalyzed epoxidation of olefins using hydrogen peroxide [J].
Anilkumar, Gopinathan ;
Bitterlich, Bianca ;
Gelalcha, Feyissa Gadissa ;
Tse, Man Kin ;
Beller, Matthias .
CHEMICAL COMMUNICATIONS, 2007, (03) :289-291
[5]  
[Anonymous], 2008, ANGEW CHEM, V120, P954, DOI DOI 10.1002/ANGE.200705115
[6]  
[Anonymous], 2006, ANGEW CHEM INT EDIT
[7]   Metal-catalyzed asymmetric epoxidations of terminal olefins using hydrogen peroxide as the oxidant [J].
Arends, Isabel W. C. E. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (38) :6250-6252
[8]   Catalytic oxidation of alcohols to carbonyl compounds with hydrogen peroxide using dinuclear iron complexes [J].
Balogh-Hergovich, É ;
Speier, G .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2005, 230 (1-2) :79-83
[9]   The selective functionalization of saturated hydrocarbons .32. Distinction between the Fe-II-Fe-IV and Fe-III-Fe-V manifolds in Gif chemistry. The importance of carboxylic acids for alkane activation. Evidence for a dimeric iron species involved in Gif-type chemistry [J].
Barton, DHR ;
Hu, B ;
Taylor, DK ;
Wahl, RUR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1996, (06) :1031-1041
[10]   THE SELECTIVE FUNCTIONALIZATION OF SATURATED-HYDROCARBONS - GIF CHEMISTRY [J].
BARTON, DHR ;
DOLLER, D .
ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (11) :504-512