Light-Induced Ruthenium-Catalyzed Nitrene Transfer Reactions: A Photochemical Approach towards N-Acyl Sulfimides and Sulfoximines

被引：206
作者：
Bizet, Vincent [1 ]
Buglioni, Laura [1 ]
Bolm, Carsten [1 ]
机构：
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52056 Aachen, Germany
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 22期
关键词：
homogeneous catalysis; nitrenes; photochemistry; ruthenium; synthetic methods; RU(SALEN)-CATALYZED ASYMMETRIC SULFIMIDATION; METAL-FREE SYNTHESIS; ALKOXYCARBONYL AZIDE; HYPERVALENT IODINE; SULFOXIDES; SULFILIMINES; IMINATION; SULFIDES; IMINOSULFURANES; PORPHYRIN;
D O I：
10.1002/anie.201310790
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
1,4,2-Dioxazol-5-ones are five-membered heterocycles known to decarboxylate under thermal or photochemical conditions, thus yielding N-acyl nitrenes. Described herein is a light-induced ruthenium-catalyzed N-acyl nitrene transfer to sulfides and sulfoxides by decarboxylation of 1,4,2-dioxazol-5-ones at room temperature, thus providing direct access to N-acyl sulfimides and sulfoximines under mild reaction conditions. In addition, a one-pot sulfur imidation/oxidation sequence catalyzed by a single ruthenium complex is reported.
引用
收藏
页码：5639 / 5642
页数：4
相关论文
共 62 条
  • [1] Kinetic studies of oxygen atom transfer reactions from trans-dioxoruthenium(VI) porphyrins to sulfides
    Abebrese, Chris
    Huang, Yan
    Pan, Alice
    Yuan, Zhibo
    Zhang, Rui
    [J]. JOURNAL OF INORGANIC BIOCHEMISTRY, 2011, 105 (12) : 1555 - 1561
  • [2] [Anonymous], 2013, ANGEW CHEM, V125, P9570, DOI DOI 10.1002/EJOC.201501611
  • [3] Iron(II)-mediated nitrene transfer from t-butyloxycarbonyl azide (BocN3) to sulfoxides, sulfides, and ketene acetals
    Bach, T
    Körber, C
    [J]. TETRAHEDRON LETTERS, 1998, 39 (28) : 5015 - 5016
  • [4] Bach T, 1999, EUR J ORG CHEM, V1999, P1033
  • [5] Role of sulfur chirality in the chemical processes of biology
    Bentley, R
    [J]. CHEMICAL SOCIETY REVIEWS, 2005, 34 (07) : 609 - 624
  • [6] Metal-free imination of sulfoxides and sulfides
    Cho, GY
    Bolm, C
    [J]. TETRAHEDRON LETTERS, 2005, 46 (46) : 8007 - 8008
  • [7] Silver-catalyzed imination of sulfoxides and sulfides
    Cho, GY
    Bolm, C
    [J]. ORGANIC LETTERS, 2005, 7 (22) : 4983 - 4985
  • [8] The key intermediate in the amination of saturated C-H bonds: synthesis, X-ray characterization and catalytic activity of Ru(TPP)(NAr)2 (Ar=3,5-(CF3)2C6H3)
    Fantauzzi, Simone
    Gallo, Emma
    Caselli, Alessandro
    Ragaini, Fabio
    Casati, Nicola
    Macchi, Piero
    Cenini, Sergio
    [J]. CHEMICAL COMMUNICATIONS, 2009, (26) : 3952 - 3954
  • [9] Catalytic, Asymmetric Synthesis of Phosphonic γ-(Hydroxyalkyl)butenolides with Contiguous Quaternary and Tertiary Stereogenic Centers
    Frings, Marcus
    Thome, Isabelle
    Schiffers, Ingo
    Pan, Fangfang
    Bolm, Carsten
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (06) : 1691 - 1700
  • [10] Synthesis of chiral sulfoximine-based thioureas and their application in asymmetric organocatalysis
    Frings, Marcus
    Thome, Isabelle
    Bolm, Carsten
    [J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2012, 8 : 1443 - 1451
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