Efficient visible light photocatalysis of [2+2] enone cycloadditions

被引:921
作者
Ischay, Michael A. [1 ]
Anzovino, Mary E. [1 ]
Du, Juana [1 ]
Yoon, Tehshik P. [1 ]
机构
[1] Univ Wisconsin, Dept Chem, Madison, WI 53706 USA
关键词
D O I
10.1021/ja805387f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report that Ru(bipy)(3)Cl(2) can serve as a visible light photocatalyst for [2+2] enone cycloadditions. A variety of aryl enones participate readily in the reaction, and the diastereoselectivity in the formation of the cyclobutane products is excellent. We propose a mechanism in which a photogenerated Ru(bipy)(3)(+) complex promotes one-electron reduction of the enone substrate, which undergoes subsequent radical anion cycloaddition. The efficiency of this process is extremely high, which allows rapid, high-yielding [2+2] cyclizations to be conducted using incident sunlight as the only source of irradiation.
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页码:12886 / +
页数:3
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共 22 条
  • [1] PHOTOCHEMICAL GENERATION OF RU(BPY)3+ AND O2-
    ANDERSON, CP
    SALMON, DJ
    MEYER, TJ
    YOUNG, RC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (06) : 1980 - 1982
  • [2] A diastereoselective metal-catalyzed [2+2] cycloaddition of bis-enones
    Baik, TG
    Luis, AL
    Wang, LC
    Krische, MJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (27) : 6716 - 6717
  • [3] PHOTOCATALYSIS OF THE PSCHORR REACTION BY TRIS-(2,2'-BIPYRIDYL)RUTHENIUM(II) IN THE PHENANTHRENE SERIES
    CANOYELO, H
    DERONZIER, A
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1984, (06): : 1093 - 1098
  • [4] PHOTO-OXIDATION OF SOME CARBINOLS BY THE RU(II) POLYPYRIDYL COMPLEX ARYL DIAZONIUM SALT SYSTEM
    CANOYELO, H
    DERONZIER, A
    [J]. TETRAHEDRON LETTERS, 1984, 25 (48) : 5517 - 5520
  • [5] Ciamician G, 1912, Science, V36, P385, DOI 10.1126/science.36.926.385
  • [6] APPLICATIONS OF LIGHT-INDUCED ELECTRON-TRANSFER REACTIONS - COUPLING OF HYDROGEN GENERATION WITH PHOTO-REDUCTION OF RUTHENIUM(II) COMPLEXES BY TRIETHYLAMINE
    DELAIVE, PJ
    SULLIVAN, BP
    MEYER, TJ
    WHITTEN, DG
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (14) : 4007 - 4008
  • [7] THE PHOTOCHEMICAL-SYNTHESIS OF FINE CHEMICALS WITH SUNLIGHT
    ESSER, P
    POHLMANN, B
    SCHARF, HD
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (20): : 2009 - 2023
  • [8] Photocatalysis for the formation of the C-C bond
    Fagnoni, Maurizio
    Dondi, Daniele
    Ravelli, Davide
    Albini, Angelo
    [J]. CHEMICAL REVIEWS, 2007, 107 (06) : 2725 - 2756
  • [9] ELECTRON-TRANSFER ASSISTED BY TRANSITION-METALS - INFLUENCE OF THE NATURE OF THE METALLIC CATION ON THE REDUCTION OF CARBONYL-COMPOUNDS IN APROTIC MEDIA
    FOURNIER, F
    FOURNIER, M
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1986, 64 (05): : 881 - 890
  • [10] Technologies for the solar photochemical and photocatalytic manufacture of specialities and commodities: A review
    Funken, KH
    Ortner, J
    [J]. ZEITSCHRIFT FUR PHYSIKALISCHE CHEMIE-INTERNATIONAL JOURNAL OF RESEARCH IN PHYSICAL CHEMISTRY & CHEMICAL PHYSICS, 1999, 213 : 99 - 105