Visible-Light Sensitization of Vinyl Azides by Transition-Metal Photocatalysis

被引:194
作者
Farney, Elliot P. [1 ]
Yoon, Tehshik P. [1 ]
机构
[1] Univ Wisconsin, Dept Chem, Madison, WI 53706 USA
基金
美国国家科学基金会;
关键词
azides; energy transfer; nitrenes; nitrogen heterocycles; photocatalysis; PHOTOLYSIS; PHOTOCHEMISTRY; DECOMPOSITION; THERMOLYSIS; 2H-AZIRINES; MECHANISM; CATALYSIS;
D O I
10.1002/anie.201308820
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Irradiation of vinyl and aryl azides with visible light in the presence of Ru photocatalysts results in the formation of reactive nitrenes, which can undergo a variety of C-N bond-forming reactions. The ability to use low-energy visible light instead of UV in the photochemical activation of azides avoids competitive photodecomposition processes that have long been a significant limitation on the synthetic use of these reactions.
引用
收藏
页码:793 / 797
页数:5
相关论文
共 41 条
[1]   Formation of Aminyl Radicals on Electron Attachment to AZT: Abstraction from the Sugar Phosphate Backbone versus One-Electron Oxidation of Guanine [J].
Adhikary, Amitava ;
Khanduri, Deepti ;
Pottiboyina, Venkata ;
Rice, Cory T. ;
Sevilla, Michael D. .
JOURNAL OF PHYSICAL CHEMISTRY B, 2010, 114 (28) :9289-9299
[2]   Acylnitrene route to vicinal amino alcohols. Application to the synthesis of (-)-bestatin and analogues [J].
Bergmeier, SC ;
Stanchina, DM .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (08) :2852-2859
[3]   Electroluminescence in ruthenium(II) complexes [J].
Bernhard, S ;
Barron, JA ;
Houston, PL ;
Abruña, HD ;
Ruglovksy, JL ;
Gao, XC ;
Malliaras, GG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (45) :13624-13628
[4]   The interplay of theory and experiment in the study of phenylnitrene [J].
Borden, WT ;
Gritsan, NP ;
Hadad, CM ;
Karney, WL ;
Kemnitz, CR ;
Platz, MS .
ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (11) :765-771
[5]   Early events in the photochemistry of aryl azides from femtosecond UV/vis spectroscopy and quantum chemical calculations [J].
Burdzinski, Gotard ;
Hackett, John C. ;
Wang, Jin ;
Gustafson, Terry L. ;
Hadad, Christopher M. ;
Platz, Matthew S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (41) :13402-13411
[6]   A biomolecule-compatible visible-light-induced azide reduction from a DNA-encoded reaction-discovery system [J].
Chen, Yiyun ;
Kamlet, Adam S. ;
Steinman, Jonathan B. ;
Liu, David R. .
NATURE CHEMISTRY, 2011, 3 (02) :146-153
[7]   Catalytic Asymmetric α-Acylation of Tertiary Amines Mediated by a Dual Catalysis Mode: N-Heterocyclic Carbene and Photoredox Catalysis [J].
DiRocco, Daniel A. ;
Rovis, Tomislav .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (19) :8094-8097
[8]   Transition metal-catalyzed synthesis of pyrroles from dienyl azides [J].
Dong, Huijun ;
Shen, Meihua ;
Redford, Joanne E. ;
Stokes, Benjamin J. ;
Pumphrey, Ashley L. ;
Driver, Tom G. .
ORGANIC LETTERS, 2007, 9 (25) :5191-5194
[9]   ENAZIDES .3. THERMOLYSIS OF ALPHA-AZIDOCINNAMATES - SYNTHESIS OF INDOL CARBOXYLATES [J].
HEMETSBE.H ;
KNITTEL, D ;
WEIDMANN, H .
MONATSHEFTE FUR CHEMIE, 1970, 101 (01) :161-&
[10]  
Hemetsberger H., 1977, J. Chem. Res. Synop, P247