Synthesis, Table of Contents Synthesis 2013; 45(19): 2689-2698DOI: 10.1055/s-0033-1338910 special topic © Georg Thieme Verlag Stuttgart · New York Visible-Light-Induced Intermolecular Atom-Transfer Radical Addition of Benzyl Halides to Olefins: Facile Synthesis of Tetrahydroquinolines Suva Paria Institut für Organische Chemie, Universität Regensburg, Universitätsstr. 31, 93053 Regensburg, Germany Fax: +49(941)9434631 Email: Oliver.Reiser@chemie.uni-regensburg.de , Michael Pirtsch Institut für Organische Chemie, Universität Regensburg, Universitätsstr. 31, 93053 Regensburg, Germany Fax: +49(941)9434631 Email: Oliver.Reiser@chemie.uni-regensburg.de , Viktor Kais Institut für Organische Chemie, Universität Regensburg, Universitätsstr. 31, 93053 Regensburg, Germany Fax: +49(941)9434631 Email: Oliver.Reiser@chemie.uni-regensburg.de , Oliver Reiser* Institut für Organische Chemie, Universität Regensburg, Universitätsstr. 31, 93053 Regensburg, Germany Fax: +49(941)9434631 Email: Oliver.Reiser@chemie.uni-regensburg.de › Author Affiliations Recommend Article Abstract Buy Article All articles of this category Abstract Cu(dap)2Cl has been utilized as a visible-light photoredox catalyst for the atom-transfer radical addition (ATRA) of benzyl halides to styrenes and silyl enol ethers. The resulting ATRA products can be readily converted into tetrahydroquinolines. Key words Key wordsvisible-light photocatalysis - atom-transfer radical addition - benzyl halide - tetrahydroquinoline Full Text References References 1a Kharasch MS, Skell PS, Fischer P. J. Am. Chem. Soc. 1948; 70: 1055 1b Kharasch MS, Jensen EV, Urry WH. Science 1945; 102: 128 2a Yorimitsu H, Nakamura T, Shinokubo H, Oshima K, Omoto K, Fujimoto H. J. Am. Chem. Soc. 2000; 122: 11041 2b Yorimitsu H, Shinokubo H, Matsubara S, Oshima K, Omoto K, Fujimoto H. J. Org. Chem. 2001; 66: 7776 3a Curran DP, Bosch E, Kaplan J, Newcomb M. J. Org. Chem. 1989; 54: 1826 3b Curran DP, Chang C.-T. J. Org. Chem. 1989; 54: 3140 3c Curran DP, Chen M.-H, Spleterz E, Seong CM, Chang C.-T. J. Am. Chem. Soc. 1989; 111: 8872 3d Curran DP, Seong CM. J. Am. Chem. Soc. 1990; 112: 9401 3e Curran DP, Tamine J. J. Org. Chem. 1991; 56: 2746 3f Curran DP, Kim D. Tetrahedron 1991; 47: 6171 4 Clark AJ. Chem. Soc. Rev. 2002; 31: 1 5 Kameyama M, Kamigata N, Kobayashi M. J. Org. Chem. 1987; 52: 3312 ; and references cited therein 6 Forti L, Ghelfi F, Libertini E, Pagnoni UM, Soragni E. Tetrahedron 1991; 53: 17761 7 Gossage RA, Van De Kuil LA, Van Koten G. Acc. Chem. Res. 1998; 31: 423 8a Matyjaszewski K, Jakubowski W, Min K, Tang W, Huang J, Braunecker WA, Tsarevsky NV. Proc. Natl. Acad. Sci. U.S.A. 2006; 103: 15309 8b Pintauer T, Matyjaszewski K. Chem. Soc. Rev. 2008; 37: 1087 8c Tsarevsky NV, Matyjaszewski K. Chem. Rev. 2007; 107: 2270 8d Wang JS, Matyjaszewski K. J. Am. Chem. Soc. 1995; 117: 5614 For recent reviews, see: 9a Teply F. Collect. Czech. Chem. Commun. 2011; 76: 859 9b Narayanam JM. R, Stephenson CR. J. Chem. Soc. Rev. 2011; 40: 102 9c Yoon TP, Ischay MA, Du J. Nat. Chem. 2010; 2: 527 9d Zeitler K. Angew. Chem. Int. Ed. 2009; 48: 9785 9e Ravelli D, Dondi D, Fagnoni M, Albini A. Chem. Soc. Rev. 2009; 38: 1999 9f Fagnoni M, Dondi D, Ravello D, Albini A. Chem. Rev. 2007; 107: 2725 10 Nguyen JD, Tucker JW, Konieczynska MD, Stephenson CR. J. J. Am. Chem. Soc. 2011; 133: 4160 11 Wallentin CJ, Nguyen JD, Finkbeiner P, Stephenson CR. J. J. Am. Chem. Soc. 2012; 134: 8875 12 Kern JM, Sauvage JP. J. Chem. Soc., Chem. Commun. 1987; 546 13 Pirtsch M, Paria S, Matsuno T, Isobe H, Reiser O. Chem. Eur. J. 2012; 18: 7336 14 Shih HW, Vander Wal MN, Grange RL, MacMillan DW. C. J. Am. Chem. Soc. 2010; 132: 13600 15 Balili MN. C, Pintauer T. Dalton Trans. 2011; 40: 3060 16 Slinker JD, Gorodetsky AA, Lowry MS, Wang J, Parker JS, Rohl R, Bernhard S, Malliaras GG. J. Am. Chem. Soc. 2004; 126: 2763 Benzyl bromide (E 1/2 = –1.85 V vs SCE in MeCN): 17a Koch DA, Henne BJ, Bartak DE. J. Electrochem. Soc. 1987; 134: 3062 17b Lawless JG, Bartak DE, Hawley MD. J. Am. Chem. Soc. 1969; 91: 7121 18 Pham PV, Nagib DA, MacMillan DW. C. Angew. Chem. Int. Ed. 2011; 50: 6119 19 Desai DG, Swami SS, Hapase SB. Synth. Commun. 1999; 29: 1033 20 Zhang F, Jin J, Zhong X, Li S, Niu J, Li R, Ma J. Green Chem. 2011; 13: 1238 21 Cromwell NH, Mercer GD. J. Am. Chem. Soc. 1957; 79: 3815 22 Guo Q.-S, Du D.-M, Xu JX. Angew. Chem. Int. Ed. 2008; 47: 759 23 Wang T, Zhuo LG, Li Z, Chen F, Ding Z, He Y, Fan QH, Xiang J, Yu ZX, Chan AS. C. J. Am. Chem. Soc. 2011; 133: 9878 Supplementary Material Supplementary Material Supporting Information
