Synlett, Inhaltsverzeichnis Synlett 2013; 24(1): 6-10DOI: 10.1055/s-0032-1317673 synpacts © Georg Thieme Verlag Stuttgart · New York Metal-Free Oxidative C(sp 3)–H Bond Couplings as Valuable Synthetic Tools for C–C Bond Formations Renate Rohlmann Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstr. 40, 48149 Münster, Germany Fax: +49(251)8333202 eMail: olga.garcia@uni-muenster.de , Olga García Mancheño* Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstr. 40, 48149 Münster, Germany Fax: +49(251)8333202 eMail: olga.garcia@uni-muenster.de › Institutsangaben Artikel empfehlen Abstract Alle Artikel dieser Rubrik Abstract Metal-free oxidative methods for the direct functionalization of C(sp 3)–H bonds to form new C–C bonds remain challenging. In this article, previous and recent results, the latter devoted to expanding the scope and synthetic applicability, on these metal-free oxidative C–C coupling reactions are highlighted. Key words Key wordsoxidation - C–H functionalization - metal-free - cross-coupling - alkenes Volltext Referenzen References 1a Dyker G. Handbook of C–H Transformations . Wiley-VCH; Weinheim: 2005 1b For a review on C–H bond functionalization in complex organic synthesis, see: Godula K, Sames D. Science 2006; 312: 67 For selected recent reviews on cross-dehydrogenative couplings, see: 2a Li C.-J. Acc. Chem. Res. 2009; 42: 335 2b Scheuermann CJ. Chem.–Asian J. 2009; 5: 436 2c Klussmann M, Sureshkumar D. Synthesis 2011; 353 2d Liu C, Zhang H, Shi W, Lei A. Chem. Rev. 2011; 111: 1780 2e Yeung CS, Dong VM. Chem. Rev. 2011; 111: 1215 For some recent mechanistic studies, see refs. 1, 2, and: 3a Boess E, Sureshkumar D, Sud A, Wirtz C, Farès C, Klussmann M. J. Am. Chem. Soc. 2011; 133: 8106 3b Klussmann M. J. Am. Chem. Soc. 2012; 134: 5317 4 Zhang Y, Li C.-J. J. Am. Chem. Soc. 2006; 128: 4242 5 Tsang AS.-K, Todd MH. Tetrahedron Lett. 2009; 50: 1199 6 Ramesh D, Ramulu U, Rajaram S, Prabhakar P, Venkateswarlu Y. Tetrahedron Lett. 2010; 51: 4898 7 Li Z, Li H, Guo X, Cao L, Yu R, Li H, Pan S. Org. Lett. 2008; 10: 803 8 Chua L, Qing F.-L. Chem. Commun. 2010; 46: 6285 9 Pintér Á, Sud A, Sureshkumar D, Klussmann M. Angew. Chem. Int. Ed. 2010; 49: 5004 10 Zhang B, Cui Y, Jiao N. Chem. Commun. 2012; 48: 4498 11 Liu Q, Li Y.-N, Zhang H.-H, Chen B, Tung C.-H, Wu L.-Z. Chem.–Eur. J. 2012; 18: 620 12a Benfatti F, Guiteras Capdevila M, Zoli L, Benedetto E, Cozzi PG. Chem. Commun. 2009; 5919 12b Zhang B, Xiang S.-K, Zhang L.-H, Cui Y, Jiao N. Org. Lett. 2012; 14: 5212 For organo- and metal co-catalyzed reactions using peroxides, see: 12c Proline–vanadium system: Sud A, Sureshkumar D, Klussmann M. Chem. Commun. 2009; 3169 12d Jørgensen–Hayashi-type catalyst–copper system: Zhang J, Tiwari B, Xing C, Chen X, Chi YR. Angew. Chem. Int. Ed. 2012; 51: 3649 For the use of activated olefins with electron-withdrawing groups for the oxidative Morita–Baylis-type reaction, see: 13a Li Z, Bohle DS, Li C.-J. Proc. Natl. Acad. Sci. U.S.A. 2006; 103: 8928 13b For the use of silyl enol ethers, see for example: Sureshkumar D, Sud A, Klussmann M. Synlett 2009; 1558 14 Song C.-X, Cai G.-X, Farrell TR, Jiang Z.-P, Li H, Gan L.-B, Shi Z.-J. Chem. Commun. 2009; 6002 15 Liu H, Cao L, Fossey JS, Deng W.-P. Chem. Commun. 2012; 48: 2674 16 Richter H, Garcίa Mancheño O. Org. Lett. 2011; 13: 6066 For previous metal-catalyzed oxidative C(sp 3)−C couplings with these types of oxidants, see: 17a Richter H, Garcίa Mancheño O. Eur. J. Org. Chem. 2010; 4460 17b Richter H, Rohlmann R, Garcίa Mancheño O. Chem.–Eur. J. 2011; 17: 11622 18 Richter H, Garcίa Mancheño O. Angew. Chem. Int. Ed. 2012; 51: 8656
