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
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共 44 条
  • [1] One-pot sequential alcohol oxidation and asymmetric α-oxyamination in aqueous media using recyclable resin-supported peptide catalyst
    Akagawa, Kengo
    Fujiwara, Takuma
    Sakamoto, Seiji
    Kudo, Kazuaki
    [J]. CHEMICAL COMMUNICATIONS, 2010, 46 (42) : 8040 - 8042
  • [2] Efficient Asymmetric α-Oxyamination of Aldehydes by Resin-Supported Peptide Catalyst in Aqueous Media
    Akagawa, Kengo
    Fujiwara, Takuma
    Sakamoto, Seiji
    Kudo, Kazuaki
    [J]. 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
    Amatore, Muriel
    Beeson, Teresa D.
    Brown, Sean P.
    MacMillan, David W. C.
    [J]. 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
    Augugliaro, Vincenzo
    Caronna, Tullio
    Loddo, Vittorio
    Marci, Giuseppe
    Palmisano, Giovanni
    Palmisano, Leonardo
    Yurdakal, Sedat
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (15) : 4640 - 4646
  • [5] Enantioselective organocatalysis using SOMO activation
    Beeson, Teresa D.
    Mastracchio, Anthony
    Hong, Jun-Bae
    Ashton, Kate
    MacMillan, David W. C.
    [J]. SCIENCE, 2007, 316 (5824) : 582 - 585
  • [6] Organocatalyzed α-Oxyamination of Aldehydes Using Anodic Oxidation
    Bui, Nhat-Nguyen
    Ho, Xuan-Huong
    Mho, Sun-il
    Jang, Hye-Young
    [J]. 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
    Bürgi, T
    Baiker, A
    [J]. JOURNAL OF PHYSICAL CHEMISTRY B, 2002, 106 (41) : 10649 - 10658
  • [8] Titanium dioxide photocatalysed alkylation of maleic acid derivatives
    Cermenati, L
    Mella, M
    Albini, A
    [J]. TETRAHEDRON, 1998, 54 (11) : 2575 - 2582
  • [9] Oxidative, photo-activated TiO2 nanoparticles in the catalytic acetylation of primary alcohols
    Chen, Chien-Tien
    Kao, Jun-Qi
    Liu, Cheng-Yuan
    Jiang, Ling-Yu
    [J]. CATALYSIS SCIENCE & TECHNOLOGY, 2011, 1 (01) : 54 - 57
  • [10] Titanium dioxide nanomaterials: Synthesis, properties, modifications, and applications
    Chen, Xiaobo
    Mao, Samuel S.
    [J]. CHEMICAL REVIEWS, 2007, 107 (07) : 2891 - 2959