Metal-Free Epoxidation of Internal and Terminal Alkenes with tert-Butyl Hydroperoxide/Isobutyraldehyde/Oxygen System

被引:10
作者
Hong, Mei [1 ]
Min, Jie [1 ]
Wang, Shifa [1 ]
机构
[1] Nanjing Forestry Univ, Coll Chem Engn, Jiangsu Key Lab Biomass Based Green Fuelsand Chem, Nanjing 210037, Jiangsu, Peoples R China
关键词
Alkene epoxidation; Isobutyraldehyde; Metal free; Molecular oxygen; Radical; MOLECULAR-OXYGEN; CATALYTIC EPOXIDATION; AEROBIC EPOXIDATION; ALLYLIC ALCOHOLS; SALEN COMPLEXES; LIQUID-PHASE; OXIDATION; OLEFINS; STYRENE; LIGANDS;
D O I
10.1002/slct.201800378
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The epoxidation of several alkenes was studied using oxygen as green oxidant, isobutyraldehyde (IBA) as co-reagent and tert-butyl hydroperoxide (TBHP) as radical initiator at mild conditions (60 degrees C, atmospheric pressure with an oxygen balloon). TBHP could accelerate the production of carbonyl radical and its peroxidation, without using a metal catalyst. The factors influencing the conversion of the substrates and selectivity of the epoxides have been well investigated. Under optimized reaction conditions, the epoxidation of linear terminal, cyclic and aromatic alkenes was evaluated. Most performed reactions were high selectivity for production of the corresponding epoxides.
引用
收藏
页码:4818 / 4821
页数:4
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共 44 条
[1]   Confinement of Mn3+ redox sites in Mn-KIT-6 and its catalytic activity for styrene epoxidation [J].
Anbazhagan, Nilamadanthai ;
Imran, Gaffar ;
Qurashi, Ahsanulhaq ;
Pandurangan, Arumugam ;
Manimaran, Shanmugam .
MICROPOROUS AND MESOPOROUS MATERIALS, 2017, 247 :190-197
[2]   Catalytic Application of Fe-doped MoO2 Tremella-Like Nanosheets [J].
Bento, Artur ;
Sanches, Anabela ;
Vaz, Pedro D. ;
Nunes, Carla D. .
TOPICS IN CATALYSIS, 2016, 59 (13-14) :1123-1131
[3]   Metal-free allylic/benzylic oxidation strategies with molecular oxygen: recent advances and future prospects [J].
Chen, Kexian ;
Zhang, Pengfei ;
Wang, Yong ;
Li, Haoran .
GREEN CHEMISTRY, 2014, 16 (05) :2344-2374
[4]   Enantioselective Epoxidation of Electron-Deficient Alkenes Catalyzed by Manganese Complexes with Chiral N4 Ligands Derived from Rigid Chiral Diamines [J].
Chen, Xiangning ;
Gao, Bao ;
Su, Yijin ;
Huang, Hanmin .
ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (15) :2535-2541
[5]   Enantioselective epoxidation of olefins with molecular oxygen catalyzed by gold(III): A dual pathway for oxygen transfer [J].
Corma, Avelino ;
Dominguez, Irene ;
Domenech, Antonio ;
Fornes, Vicente ;
Gomez-Garcia, Carlos J. ;
Rodenas, Tania ;
Sabater, Maria J. .
JOURNAL OF CATALYSIS, 2009, 265 (02) :238-244
[6]   Asymmetric Nucleophilic Catalysis with an Octahedral Chiral-at-Metal Iridium(III) Complex [J].
Cruchter, Thomas ;
Medvedev, Michael G. ;
Shen, Xiaodong ;
Mietke, Thomas ;
Harms, Klaus ;
Marsch, Michael ;
Meggers, Eric .
ACS CATALYSIS, 2017, 7 (08) :5151-5162
[7]   Environmentally Benign Bioderived Carbon Microspheres-Supported Molybdena Nanoparticles as Catalyst for the Epoxidation Reaction [J].
Doke, Dhananjay S. ;
Umbarkar, Shubhangi B. ;
Gawande, Manoj B. ;
Zbori, Radek ;
Biradar, Ankush V. .
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2017, 5 (01) :904-910
[8]   The importance of Green Chemistry in Process Research and Development [J].
Dunn, Peter J. .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (04) :1452-1461
[9]   Highly efficient asymmetric epoxidation of olefins with a chiral manganese-porphyrin covalently bound to mesoporous SBA-15: Support effect [J].
Farokhi, Afsaneh ;
Monfared, Hassan Hosseini .
JOURNAL OF CATALYSIS, 2017, 352 :229-238
[10]   Bio-inspired Mo(II) complexes as active catalysts in homogeneous and heterogeneous olefin epoxidation [J].
Fernandes, Cristina I. ;
Silva, Nuno U. ;
Vaz, Pedro D. ;
Nunes, Teresa G. ;
Nunes, Carla D. .
APPLIED CATALYSIS A-GENERAL, 2010, 384 (1-2) :84-93