Decatungstate As Photoredox Catalyst: Benzylation of Electron-Poor Olefins

被引:66
作者
Montanaro, Sara [1 ]
Ravelli, Davide [1 ]
Merli, Daniele [1 ]
Fagnoni, Maurizio [1 ]
Albini, Angelo [1 ]
机构
[1] Univ Pavia, Dept Chem, PhotoGreen Lab, I-27100 Pavia, Italy
关键词
EXCITED-STATE; PHOTOCATALYZED OXIDATION; FUNCTIONALIZATION; REACTIVITY; ACTIVATION; MECHANISM; SECONDARY; EXCIPLEX; ALKENES; KETONES;
D O I
10.1021/ol301900p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Excited tetrabutylammonium decatungstate (TBADT), known to activate a variety of compounds via hydrogen atom transfer (HAT), has now been applied as a photoredox catalyst for the effective oxidative cleavage of benzyl silanes and radical benzylation of reducible olefins occurring in isolated yields from poor to excellent.
引用
收藏
页码:4218 / 4221
页数:4
相关论文
共 51 条
  • [1] C-H Bond Arylations and Benzylations on Oxazol(in)es with a Palladium Catalyst of a Secondary Phosphine Oxide
    Ackermann, Lutz
    Barfuesser, Sebastian
    Kornhaass, Christoph
    Kapdi, Anant R.
    [J]. ORGANIC LETTERS, 2011, 13 (12) : 3082 - 3085
  • [2] Albini A, 2005, MOL SUPRAM PHOTOCHEM, V12, P453
  • [3] Tetrabutylammonium Decatungstate (Chemo)selective Photocatalyzed, Radical C-H Functionalization in Amides
    Angioni, Simone
    Ravelli, Davide
    Emma, Daniele
    Dondi, Daniele
    Fagnoni, Maurizio
    Albini, Angelo
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (14-15) : 2209 - 2214
  • [4] PHOTOSENSITIZED (ELECTRON-TRANSFER) [2E+4E] DIMERIZATION AND CROSS-CYCLOADDITION OF PHENYLATED OLEFINS - TRAPPING THE INTERMEDIATE
    ARNOLD, DR
    BORG, RM
    ALBINI, A
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (03) : 138 - 139
  • [5] TITANIUM-DIOXIDE PHOTOCATALYZED OXIDATION OF BENZYLTRIMETHYLSILANES IN THE PRESENCE OF SILVER SULFATE
    BACIOCCHI, E
    ROL, C
    ROSATO, GC
    SEBASTIANI, GV
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (01) : 59 - 60
  • [6] Reactivity of benzyl radicals: The trapping of primary, secondary and tertiary benzyl radicals with heterocyclic bases
    Brivio, Luigi
    Caronna, Tullio
    Fontana, Francesca
    Gambarotti, Cristian
    Mele, Andrea
    Natali Sora, Isabella
    Punta, Carlo
    Recupero, Francesco
    [J]. JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2010, 214 (01) : 112 - 114
  • [7] Solar light induced carbon-carbon bond formation via TiO2 photocatalysis
    Cermenati, L
    Richter, C
    Albini, A
    [J]. CHEMICAL COMMUNICATIONS, 1998, (07) : 805 - 806
  • [8] SET AND EXCIPLEX PATHWAYS IN THE PHOTOCHEMICAL-REACTIONS BETWEEN AROMATIC KETONES AND BENZYLSILANE AND STANNANE DERIVATIVES
    CERMENATI, L
    FRECCERO, M
    VENTURELLO, P
    ALBINI, A
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (30) : 7869 - 7876
  • [9] NUCLEOPHILE-ASSISTED CLEAVAGE OF SILANE CATION RADICALS
    DINNOCENZO, JP
    FARID, S
    GOODMAN, JL
    GOULD, IR
    TODD, WP
    MATTES, SL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (24) : 8973 - 8975
  • [10] Photomediated synthesis of β-alkylketones from cycloalkanes
    Dondi, Daniele
    Cardarelli, Anna Maria
    Fagnoni, Maurizio
    Albini, Angelo
    [J]. TETRAHEDRON, 2006, 62 (23) : 5527 - 5535