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Pure Appl. Chem., 2007, Vol. 79, No. 11, pp. 1949-1958

http://dx.doi.org/10.1351/pac200779111949

Photochemically induced radical addition of tertiary amines to C=C and C=O double bonds: A green chemistry contribution to organic synthesis

Norbert Hoffmann

Selective Reactions and Applications Laboratory, UMR 6519 CNRS and University of Reims Champagne-Ardenne, UFR Sciences, B.P. 1039, F-51687 Reims, Cedex 02, France

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  • Kisch Horst: Halbleiterphotokatalyse - mechanistische und präparative Aspekte. Angew. Chem. 2013, 125, 842. <http://dx.doi.org/10.1002/ange.201201200>
  • Kisch Horst: Semiconductor Photocatalysis-Mechanistic and Synthetic Aspects. Angew. Chem. Int. Ed. 2013, 52, 812. <http://dx.doi.org/10.1002/anie.201201200>
  • Zhu Shaoqun, Das Arindam, Bui Lan, Zhou Hanjun, Curran Dennis P., Rueping Magnus: Oxygen Switch in Visible-Light Photoredox Catalysis: Radical Additions and Cyclizations and Unexpected C–C-Bond Cleavage Reactions. J. Am. Chem. Soc. 2013, 135, 1823. <http://dx.doi.org/10.1021/ja309580a>
  • Wang Wei, Zhang Wen-Jie, Wang Lei, Quah Ching Kheng, Fun Hoong-Kun, Xu Jian-Hua, Zhang Yan: Photoinduced Reactions of para-Quinones with Bicyclopropylidene Leading to Diverse Polycyclic Compounds with Spirocyclopropanes. J. Org. Chem. 2013, 78, 6211. <http://dx.doi.org/10.1021/jo4008767>
  • Zhou Hongxia, Lu Ping, Gu Xiangyong, Li Pixu: Visible-Light-Mediated Nucleophilic Addition of an α-Aminoalkyl Radical to Isocyanate or Isothiocyanate. Org. Lett. 2013, 15, 5646. <http://dx.doi.org/10.1021/ol402573j>
  • Gassama Abdoulaye, Ernenwein Cédric, Youssef Ali, Agach Mickaël, Riguet Emmanuel, Marinković Siniša, Estrine Boris, Hoffmann Norbert: Sulfonated surfactants obtained from furfural. Green Chem. 2013, 15, 1558. <http://dx.doi.org/10.1039/c3gc00062a>
  • Vila Carlos, Rueping Magnus: Visible-light mediated heterogeneous C–H functionalization: oxidative multi-component reactions using a recyclable titanium dioxide (TiO2) catalyst. Green Chem. 2013, 15, 2056. <http://dx.doi.org/10.1039/c3gc40587g>
  • Wu Dong-Dong, Huang Cheng-Mei, Wu Yi-Han, Fun Hoong-Kun, Xu Jian-Hua, Zhang Yan: Acid-mediated transformation of spirocyclopropyl oxetanes: a facile approach to spirocyclopropyl butenolides and γ-butyrolactones. RSC Adv. 2013, 3, 7529. <http://dx.doi.org/10.1039/c3ra00178d>
  • Yamaguchi Junichiro, Yamaguchi Atsushi D., Itami Kenichiro: Funktionalisierung von C-H-Bindungen: neue Synthesemethoden für Naturstoffe und Pharmazeutika. Angew. Chem. 2012, 124, 9092. <http://dx.doi.org/10.1002/ange.201201666>
  • Yamaguchi Junichiro, Yamaguchi Atsushi D., Itami Kenichiro: CH Bond Functionalization: Emerging Synthetic Tools for Natural Products and Pharmaceuticals. Angew. Chem. Int. Ed. 2012, 51, 8960. <http://dx.doi.org/10.1002/anie.201201666>
  • Wu Dong-Dong, He Ming-Tao, Liu Qi-Di, Wang Wei, Zhou Jie, Wang Lei, Fun Hoong-Kun, Xu Jian-Hua, Zhang Yan: Photoinduced reactions of bicycloalkylidenes with isatin and isoquinolinetrione. Biomol Chem 2012, 10, 3626. <http://dx.doi.org/10.1039/c2ob07158d>
  • Hoffmann Norbert: Photochemical reactions of aromatic compounds and the concept of the photon as a traceless reagent. Photochem. Photobiol. Sci. 2012, 11, 1613. <http://dx.doi.org/10.1039/c2pp25074h>
  • Yavorskyy Alexander, Shvydkiv Oksana, Nolan Kieran, Hoffmann Norbert, Oelgemöller Michael: Photosensitized addition of isopropanol to furanones in a continuous-flow dual capillary microreactor. Tetrahedron Letters 2011, 52, 278. <http://dx.doi.org/10.1016/j.tetlet.2010.11.018>
  • Jahjah Rabih, Gassama Abdoulaye, Dumur Frédéric, Marinković Siniša, Richert Sabine, Landgraf Stephan, Lebrun Aurélien, Cadiou Cyril, Sellès Patrice, Hoffmann Norbert: Photochemical Electron Transfer Mediated Addition of Naphthylamine Derivatives to Electron-Deficient Alkenes. J Org Chern 2011, 76, 7104. <http://dx.doi.org/10.1021/jo201080m>
  • Kamon Takuma, Irifune Yayoi, Tanaka Tetsuaki, Yoshimitsu Takehiko: Total Synthesis of (±)-Kainic Acid: A Photochemical C–H Carbamoylation Approach. Org Lett 2011, 13, 2674. <http://dx.doi.org/10.1021/ol200772f>
  • Hari Durga Prasad, König Burkhard: Eosin Y Catalyzed Visible Light Oxidative C–C and C–P bond Formation. Org Lett 2011, 13, 3852. <http://dx.doi.org/10.1021/ol201376v>
  • Shvydkiv Oksana, Yavorskyy Alexander, Tan Su Bee, Nolan Kieran, Hoffmann Norbert, Youssef Ali, Oelgemöller Michael: Microphotochemistry: a reactor comparison study using the photosensitized addition of isopropanol to furanones as a model reaction. Photochem Photobiol Sci 2011, 10, 1399. <http://dx.doi.org/10.1039/c1pp05024a>
  • Gallagher Sonia, Hatoum Fadi, Zientek Nicolai, Oelgemöller Michael: Photodecarboxylative additions of N-protected α-amino acids to N-methylphthalimide. Tetrahetron Lett 2010, 51, 3639. <http://dx.doi.org/10.1016/j.tetlet.2010.05.020>
  • Coyle Emma E., Joyce Kieran, Nolan Kieran, Oelgemöller Michael: Green photochemistry: the use of microemulsions as green media in photooxygenation reactions. Green Chem 2010, 12, 1544. <http://dx.doi.org/10.1039/c004869k>
  • Shvydkiv Oksana, Yavorskyy Alexander, Nolan Kieran, Youssef Ali, Riguet Emmanuel, Hoffmann Norbert, Oelgemöller Michael: Photosensitized addition of isopropanol to furanones in a 365 nm UV-LED microchip. Photochem Photobiol Sci 2010, 9, 1601. <http://dx.doi.org/10.1039/c0pp00223b>
  • Haggiage Elodie, Coyle Emma E., Joyce Kieran, Oelgemöller Michael: Green photochemistry: solarchemical synthesis of 5-amido-1,4-naphthoquinones. Green Chem 2009, 11, 318. <http://dx.doi.org/10.1039/b816676e>
  • Murphy Brian, Goodrich Peter, Hardacre Christopher, Oelgemöller Michael: Green photochemistry: photo-Friedel–Crafts acylations of 1,4-naphthoquinone in room temperature ionic liquids. Green Chem 2009, 11, 1867. <http://dx.doi.org/10.1039/b913252j>
  • Hoffmann Norbert: Efficient photochemical electron transfer sensitization of homogeneous organic reactions. J Photochem Photobiol C Photochem Rev 2008, 9, 43. <http://dx.doi.org/10.1016/j.jphotochemrev.2008.04.002>
  • Tanko J. M.: Reaction mechanisms : Part (i) Radical and radical ion reactions. Annu Rep Prog Chem Sect B 2008, 104, 234. <http://dx.doi.org/10.1039/b801277f>