Download PDF
Synlett 2009(19): 3135-3138  
DOI: 10.1055/s-0029-1218293
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Catalytic Intermolecular Hydroamination of Vinyl Ethers

Nirmal K. Pahadi*, Jon A. Tunge*
Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045-7582, USA
Fax: +1(785)8645396; e-Mail: tunge@ku.edu;
Further Information

Publication History

Received 30 July 2009
Publication Date:
21 October 2009 (online)

    Permissions and Reprints All articles of this category

Abstract

This manuscript details the development of a palladium-catalyzed hydroamination of vinyl ethers. It is proposed that palladium catalyzes the hydroamination via Brønsted base catalysis, where palladium is protonated by the relatively acidic sulfonamide to generate a palladium hydride as well as the active anionic sulfonamide nucleophile. Thus, this process is distinct from known palladium-catalyzed hydroaminations of styrene derivatives that utilize less acidic amines.

Key words

hydroamination - vinyl ether - palladium - sulfonamide

    References

  • 1a Mueller TE. Hultzsch KC. Yus M. Foubelo F. Tada M. Chem. Rev.  2008,  108:  3795 
    Google Scholar
  • 1b Widenhoefer RA. Han X. Eur. J. Org. Chem.  2006,  4555 
    Google Scholar
  • 1c Hazari N. Mountford P. Acc. Chem. Res.  2005,  38:  839 
    Google Scholar
  • 1d Hultzsch KC. Org. Biomol. Chem.  2005,  3:  1819 
    Google Scholar
  • 1e Hong S. Marks TJ. Acc. Chem. Res.  2004,  37:  673 
    Google Scholar
  • 1f Mueller TE. Beller M. Chem. Rev.  1998,  98:  675 
    Google Scholar
  • 2a Ohimiya H. Moriya T. Sawamura M. Org. Lett.  2009,  11:  2145 
    Google Scholar
  • 2b Hesp KD. Stradiotto M. Org. Lett.  2009,  11:  1449 
    Google Scholar
  • 2c Biyikal M. Lohnwitz K. Roesky PW. Bechert S. Synlett  2008,  3106 
    Google Scholar
  • 2d Graebe K. Pohlki F. Doye S. Eur. J. Org. Chem.  2008,  4815 
    Google Scholar
  • 2e Majumder S. Odom AL. Organometallics  2008,  27:  1174 
    Google Scholar
  • 2f Liu Z. Hartwig JF. J. Am. Chem. Soc.  2008,  130:  1570 
    Google Scholar
  • For recent acid-catalyzed hydroaminations, see:
  • 3a Li Z. Zhang J. Brouwer C. Yang C.-G. Reich NW. He C. Org. Lett.  2006,  8:  4175 
    Google Scholar
  • 3b Motokura K. Nakagiri N. Mori K. Mizugaki T. Ebitani K. Jitsukawa K. Kaneda K. Org. Lett.  2006,  8:  4617 
    Google Scholar
  • 3c Rosenfeld DC. Shekhar S. Takemiya A. Utsunomiya M. Hartwig JF. Org. Lett.  2006,  8:  4179 
    Google Scholar
  • 3d Schlummer B. Hartwig JF. Org. Lett.  2002,  4:  1471 
    Google Scholar
  • 3e Colinas PA. Brave RD. Org. Lett.  2003,  5:  4509 
    Google Scholar
  • 3f Toshima K. Nagai H. Ushiki Y. Matsumura S. Synlett  1998,  1007 
    Google Scholar
  • 3g Karshtedt D. Bell AT. Tilly TD. J. Am. Chem. Soc.  2005,  127:  12640 
    Google Scholar
  • 3h Widenhoefer R. Angew. Chem. Int. Ed.  2006,  45:  1747 
    Google Scholar
  • 3i Jiao P. Nakashima D. Yamamoto H. Angew. Chem. Int. Ed.  2008,  47:  2411 
    Google Scholar
  • 4a Kawatsura M. Hartwig JF. Organometallics  2001,  20:  1960 
    Google Scholar
  • 4b Fadini L. Togni A. Chem. Commun.  2003,  30 
    Google Scholar
  • 4c Li K. Hii KK. Chem. Commun.  2003,  1132 
    Google Scholar
  • 4d Munro-Leighton C. Blue ED. Gunnoe TB. J. Am. Chem. Soc.  2006,  128:  1446 
    Google Scholar
  • 5a Zhou J. Hartwig JF. J. Am. Chem. Soc.  2008,  130:  12220 
    Google Scholar
  • 5b Giner X. Najera C. Org. Lett.  2008,  10:  2919 
    Google Scholar
  • 5c Qin H. Yamagiwa N. Matsunaga S. Shibasaki M.
    J. Am. Chem. Soc.  2006,  128:  1611 
    Google Scholar
  • 6a Johns AM. Utsunomiya M. Incarvito CD. Hartwig JF. J. Am. Chem. Soc.  2006,  128:  1828 
    Google Scholar
  • 6b Utsunomiya M. Hartwig JF. J. Am. Chem. Soc.  2003,  125:  14286 
    Google Scholar
  • 6c Nettekoven U. Hartwig JF. J. Am. Chem. Soc.  2002,  124:  1166 
    Google Scholar
  • 6d Kawatsura M. Hartwig JF. J. Am. Chem. Soc.  2000,  122:  9546 
    Google Scholar
  • 6e Utsunomiya M. Hartwig JF.
    J. Am. Chem. Soc.  2004,  126:  2702 
    Google Scholar
  • 6f Utsunomiya M. Kuwano R. Motoi K. Hartwig JF. J. Am. Chem. Soc.  2003,  125:  5608 
    Google Scholar
  • 7a Tada M. Shimamoto M. Sasaki T. Iwasawa Y. Chem. Commun.  2004,  2562 
    Google Scholar
  • 7b Penzien J. Su RQ. Muller TE. J. Mol. Catal. A.  2002,  182-183:  489 
    Google Scholar
  • 7c Vogels CM. Hayes PG. Shaver MP. Westcott SA. Chem. Commun.  2000,  51 
    Google Scholar
  • 8 Colinas PA. Bravo RD. Org. Lett.  2003,  5:  4509 
    CrossrefGoogle Scholar
  • 9 Sherry BD. Loy RN. Toste FD. J. Am. Chem. Soc.  2004,  126:  4510 
    CrossrefGoogle Scholar
  • 10 Cochran B. Michael FE. J. Am. Chem. Soc.  2008,  130:  2786 
    CrossrefGoogle Scholar
  • 11 Shainyan BA. Grigor’eva AA. Russ. J. Org. Chem.  2001,  37:  1177 
    CrossrefGoogle Scholar
  • 12 Knight JG. Ainge SW. Harm AM. Harwood SJ. Maughan HI. Armour DR. Hollinshead DM. Jaxa-Chamiec AA. J. Am. Chem. Soc.  2000,  122:  2944 
    Google Scholar
  • 13 Trost BM. Chem. Eur. J.  1998,  4:  2405 
    CrossrefGoogle Scholar
  • 14 Luo S. Jordan RF. J. Am. Chem. Soc.  2006,  128:  12072 
    CrossrefGoogle Scholar