Green organophotocatalysis. TiO2-induced enantioselective α-oxyamination of aldehydes

被引:36
作者
Ho, Xuan-Huong [1 ]
Kang, Min-Jung [1 ]
Kim, Seung-Joo [1 ]
Park, Eun Duck [1 ]
Jang, Hye-Young [1 ]
机构
[1] Ajou Univ, Div Energy Syst Res, Suwon 443749, South Korea
关键词
AROMATIC ALCOHOLS; AEROBIC OXIDATION; SOMO CATALYSIS; TIO2; LIGHT; ORGANOCATALYSIS; PHOTOCATALYSIS; HYDROGENATION; ALKYLATION; ARYLATION;
D O I
10.1039/c1cy00183c
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Asymmetric C-O bond formation with various aldehydes is examined under conditions of environmentally benign photo-organocatalysis. A heterogeneous TiO2 photocatalyst is used as a photooxidant in place of toxic and expensive chemical oxidants, for the first time in chemo- and stereoselective bond formation.
引用
收藏
页码:923 / 926
页数:4
相关论文
共 44 条
[1]   One-pot sequential alcohol oxidation and asymmetric α-oxyamination in aqueous media using recyclable resin-supported peptide catalyst [J].
Akagawa, Kengo ;
Fujiwara, Takuma ;
Sakamoto, Seiji ;
Kudo, Kazuaki .
CHEMICAL COMMUNICATIONS, 2010, 46 (42) :8040-8042
[2]   Efficient Asymmetric α-Oxyamination of Aldehydes by Resin-Supported Peptide Catalyst in Aqueous Media [J].
Akagawa, Kengo ;
Fujiwara, Takuma ;
Sakamoto, Seiji ;
Kudo, Kazuaki .
ORGANIC LETTERS, 2010, 12 (08) :1804-1807
[3]   Enantioselective Linchpin Catalysis by SOMO Catalysis: An Approach to the Asymmetric α-Chlorination of Aldehydes and Terminal Epoxide Formation [J].
Amatore, Muriel ;
Beeson, Teresa D. ;
Brown, Sean P. ;
MacMillan, David W. C. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5121-5124
[4]   Oxidation of aromatic alcohols in irradiated aqueous suspensions of commercial and home-prepared ruffle TiO2:: A selectivity study [J].
Augugliaro, Vincenzo ;
Caronna, Tullio ;
Loddo, Vittorio ;
Marci, Giuseppe ;
Palmisano, Giovanni ;
Palmisano, Leonardo ;
Yurdakal, Sedat .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (15) :4640-4646
[5]   Enantioselective organocatalysis using SOMO activation [J].
Beeson, Teresa D. ;
Mastracchio, Anthony ;
Hong, Jun-Bae ;
Ashton, Kate ;
MacMillan, David W. C. .
SCIENCE, 2007, 316 (5824) :582-585
[6]   Organocatalyzed α-Oxyamination of Aldehydes Using Anodic Oxidation [J].
Bui, Nhat-Nguyen ;
Ho, Xuan-Huong ;
Mho, Sun-il ;
Jang, Hye-Young .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (31) :5309-5312
[7]   In situ infrared spectroscopy of catalytic solid-liquid interfaces using phase-sensitive detection:: Enantioselective hydrogenation of a pyrone over Pd/TiO2 [J].
Bürgi, T ;
Baiker, A .
JOURNAL OF PHYSICAL CHEMISTRY B, 2002, 106 (41) :10649-10658
[8]   Titanium dioxide photocatalysed alkylation of maleic acid derivatives [J].
Cermenati, L ;
Mella, M ;
Albini, A .
TETRAHEDRON, 1998, 54 (11) :2575-2582
[9]   Oxidative, photo-activated TiO2 nanoparticles in the catalytic acetylation of primary alcohols [J].
Chen, Chien-Tien ;
Kao, Jun-Qi ;
Liu, Cheng-Yuan ;
Jiang, Ling-Yu .
CATALYSIS SCIENCE & TECHNOLOGY, 2011, 1 (01) :54-57
[10]   Titanium dioxide nanomaterials: Synthesis, properties, modifications, and applications [J].
Chen, Xiaobo ;
Mao, Samuel S. .
CHEMICAL REVIEWS, 2007, 107 (07) :2891-2959