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Synthesis 2011(16): 2579-2589  
DOI: 10.1055/s-0030-1260087
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart ˙ New York

Palladium-Catalyzed Ligand-Directed Oxidative Functionalization of Cyclopropanes

Asako Kubota, Melanie S. Sanford*
University of Michigan, Department of Chemistry, 930 N. University Ave, Ann Arbor, MI 48109, USA
Fax: +1(734)6474865; e-Mail: mssanfor@umich.edu;
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Publikationsverlauf

Received 15 March 2011
Publikationsdatum:
08. Juli 2011 (online)

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Abstract

This report describes the palladium-catalyzed functionalization of cyclopropanes containing oxazoline, oxime ether, and pyridine directing groups. Three different oxidants were examined in these studies: IOAc, PhI(OAc)2, and benzoquinone. The reactions yielded products derived from 2˚ sp³ C-H functionalization and/or C-C activation of the cyclopropane ring. The outcome and the product distributions were highly dependent on the structure of the substrate and the nature of the oxidant.

Key words

cyclopropane - C-H functionalization - palladium - cleavage - homogeneous catalysis

    References

  • For some recent reviews on C-H functionalization, see:
  • 1a Kakiuchi F. Chatani N. Adv. Synth. Catal.  2003,  345:  1077 
    Google Scholar
  • 1b Diaz-Requejo MM. Perez PJ. Chem. Rev.  2008,  108:  3379 
    Google Scholar
  • 1c Jazzar R. Hitce J. Renaudat A. Sofack-Kreutzer J. Baudoin O. Chem. Eur. J.  2010,  16:  2654 
    Google Scholar
  • 1d Colby DA. Bergman RG. Ellman JA. Chem. Rev.  2010,  110:  624 
    Google Scholar
  • 1e Doyle MP. Duffy R. Ratnikov M. Zhou L. Chem. Rev.  2010,  110:  704 
    Google Scholar
  • 1f Mkhalid IAI. Barnard JH. Marder TB. Murphy JM. Hartwig JF. Chem. Rev.  2010,  110:  890 
    Google Scholar
  • 1g C-H Activation, In Topics in Current Chemistry   Vol. 292:  Yu JQ. Shi Z. Springer; Berlin: 2010. 
    Google Scholar
  • 2 Lyons TW. Sanford MS. Chem. Rev.  2010,  110:  1147 
    Google Scholar
  • 3 Desai LV. Hull KL. Sanford MS. J. Am. Chem. Soc.  2004,  126:  9542 
    CrossrefPubMedGoogle Scholar
  • 4 Kalyani D. Deprez NR. Desai LV. Sanford MS.
    J. Am. Chem. Soc.  2005,  127:  7330 
    CrossrefPubMedGoogle Scholar
  • 5a Zaitsev VG. Shabashov D. Daugulis O. J. Am. Chem. Soc.  2005,  127:  13154 
    Google Scholar
  • 5b Shabashov D. Daugulis O.
    J. Am. Chem. Soc.  2010,  132:  3965 
    Google Scholar
  • 6 Giri R. Chen X. Yu JQ. Angew. Chem. Int. Ed.  2005,  44:  2112 
    CrossrefPubMedGoogle Scholar
  • 7 Giri R. Maugel N. Li JJ. Wang DH. Breazzano SP. Saunders LB. Yu JQ. J. Am. Chem. Soc.  2007,  129:  3510 
    Google Scholar
  • 8 Wang DH. Wasa M. Giri R. Yu JQ. J. Am. Chem. Soc.  2008,  130:  7190 
    CrossrefGoogle Scholar
  • 9 Wasa M. Engle KM. Yu JQ. J. Am. Chem. Soc.  2010,  132:  3680 
    CrossrefPubMedGoogle Scholar
  • 10 Stowers KJ. Fortner KC. Sanford MS. J. Am. Chem. Soc.  2011,  133:  6541 
    CrossrefGoogle Scholar
  • 11 The Chemistry of the Cyclopropyl Group   Rappoport Z. Wiley; Chichester: 1987. 
    Google Scholar
  • For selected reviews on synthetic applications of cyclopropanes, see:
  • 12a Reissig HU. Zimmer R. Chem. Rev.  2003,  103:  1151 
    Google Scholar
  • 12b Yu M. Pagenkopf BL. Tetrahedron  2005,  61:  321 
    Google Scholar
  • 12c Carson CA. Kerr MA. Chem. Soc. Rev.  2009,  38:  3051 
    Google Scholar
  • 13a Dick AR. Hull KL. Sanford MS. J. Am. Chem. Soc.  2004,  126:  2300 
    Google Scholar
  • 13b Kalyani D. Sanford MS. Org. Lett.  2005,  7:  4149 
    Google Scholar
  • 13c Desai LV. Malik HA. Sanford MS. Org. Lett.  2006,  8:  1141 
    Google Scholar
  • 13d Desai LV. Stowers KJ. Sanford MS. J. Am. Chem. Soc.  2008,  130:  13285 
    Google Scholar
  • 13e Stowers KJ. Sanford MS. Org. Lett.  2009,  11:  4584 
    Google Scholar
  • 13f Neufeldt SR. Sanford MS. Org. Lett.  2010,  12:  532 
    Google Scholar
  • 14a Yoneyama T. Crabtree RH. J. Mol. Catal. A: Chem.  1996,  108:  35 
    Google Scholar
  • 14b Gou FR. Wang XC. Huo PF. Bi HP. Guan ZH. Liang YM. Org. Lett.  2009,  11:  5726 
    Google Scholar
  • 14c Mutule I. Suna E. Olofsson K. Pelcman B. J. Org. Chem.  2009,  74:  7195 
    Google Scholar
  • 15 He Z. Yudin AK. Org. Lett.  2006,  8:  5829 
    CrossrefGoogle Scholar
  • 16a Li Y. Song D. Dong VM. J. Am. Chem. Soc.  2008,  130:  2962 
    Google Scholar
  • 16b Wang W. Wang F. Shi M. Organometallics  2010,  29:  928 
    Google Scholar
  • 17 Wallace DJ. Chen CY. Tetrahedron Lett.  2002,  43:  6987 
    CrossrefGoogle Scholar
  • 18 Wilhelm D. Backvall JE. Nordberg RE. Norin T. Organometallics  1985,  4:  1296 
    Google Scholar
  • 19a Charette AB. Juteau H. Lebel H. Molinaro C. J. Am. Chem. Soc.  1998,  120:  11943 
    Google Scholar
  • 19b Cryle MJ. Ortiz de Montellano PR. De Voss JJ. J. Org. Chem.  2005,  70:  2455 
    Google Scholar
  • 20 Denmark SE. Yang SM. J. Am. Chem. Soc.  2002,  124:  2102 
    Google Scholar