PDF herunterladen
Synlett 2009(2): 287-291  
DOI: 10.1055/s-0028-1087671
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Reduction of Phosphinites, Phosphinates, and Related Species with DIBAL-H

Carl A. Busacca*, Teresa Bartholomeyzik, Sreedhar Cheekoori, Ravinder Raju, Magnus Eriksson, Suresh Kapadia, Anjan Saha, Xingzhong Zeng, Chris H. Senanayake
Department of Chemical Development, Boehringer-Ingelheim Pharmaceuticals Inc., 900 Ridgebury Rd., Ridgefield, CT 06877, USA
e-Mail: carl.busacca@boehringer-ingelheim.com;
Weitere Informationen

Publikationsverlauf

Received 1 September 2008
Publikationsdatum:
15. Januar 2009 (online)

   Lizenzen und Reprints Alle Artikel dieser Rubrik
Preview

Abstract

Diisobutylaluminium hydride has been found to be an excellent reducing agent for phosphinites, phosphinates, and chlorophosphines. By performing reductions in situ, direct synthesis of secondary phosphine boranes from Grignard reagents has been achieved without isolation or purification of any intermediates.

Key words

phosphorus - phosphines - phosphine boranes - reductions

    References

  • 1a Busacca CA. Lorenz JC. Grinberg N. Haddad N. Hrapchak M. Latli B. Lee H. Sabila P. Saha A. Sarvestani M. Shen S. Varsolona R. Wei X. Senanayake CH. Org. Lett.  2007,  7:  4277 
    Suche in Google Scholar
  • 1b Busacca CA. inventors; US  7 256 314. 
  • 2 Busacca CA. Raju R. Grinberg N. Haddad N. James-Jones P. Lee H. Lorenz JC. Saha A. Senanayake CH. J. Org. Chem.  2008,  73:  1524 
    CrossrefSuche in Google Scholar
  • 3 Busacca CA. Lorenz JC. Sabila P. Haddad N. Senanayake CH. Org. Synth.  2007,  84:  242 
    Suche in Google Scholar
  • For recent examples, see:
  • 4a Ito H. Watanabe A. Sawamaura M. Org. Lett.  2005,  7:  1869 
    Suche in Google Scholar
  • 4b Matsumura K. Shimizu H. Saito T. Kumobayashi H. Adv. Synth. Catal.  2003,  345:  180 
    Suche in Google Scholar
  • 4c Wolfe B. Livinghouse T. J. Am. Chem. Soc.  1998,  120:  5116 
    Suche in Google Scholar
  • 5a Stankevic M. Pietrusiewicz KM. J. Org. Chem.  2007,  72:  816 
    Suche in Google Scholar
  • 5b Stankevic M. Andrijewski G. Pietrusiewicz KM. Synlett  2004,  311 
  • 5c Brunel JM. Faure B. Maffei M. Coord. Chem. Rev.  1998,  180:  665 
    Suche in Google Scholar
  • 5d Imamoto T. Matsuo M. Nonomura T. Kishikawa K. Yanagawa M. Heteroat. Chem.  1993,  4:  475 
    Suche in Google Scholar
  • For the reduction of chlorophosphine-borane complexes with a variety of reducing agents, see:
  • 6a Lam H. Aldous DJ. Hii KK. Tetrahedron Lett.  2003,  44:  5213 
    Suche in Google Scholar
  • 7a Dodds DL. Haddow MF. Orpen AG. Pringle PG. Woodward G. Organometallics  2006,  25:  5937 
    Suche in Google Scholar
  • 7b Kuchen W. Buchwald H. Chem. Ber.  1959,  227 
  • For reviews, see:
  • 8a Engel R. Cohen JLI. Synthesis of Carbon-Phosphorus Bonds   CRC Press; Boca Raton: 1988.  Chap. 3 and 6.
  • 8b Bhattacharya AK. Thyagarajan G. Chem. Rev.  1981,  81:  415 
    Suche in Google Scholar
  • 9a Han L.-B. Zhao Z.-Q. J. Org. Chem.  2005,  70:  10121 
    Suche in Google Scholar
  • 9b Benschop HP. Platenburg DHJM. J. Chem. Soc., Chem. Commun.  1970,  17:  1098 
    Suche in Google Scholar
  • Copper:
  • 10a Rao H. Jin Y. Fu H. Jiang Y. Zhao Y. Chem. Eur. J.  2006,  12:  3636 
    Suche in Google Scholar
  • Palladium:
  • 10b Beletskaya IP. Neganova EG. Veits YA. Russ. J. Org. Chem.  2004,  40:  1782 
    Suche in Google Scholar
  • 10c Schuman M. Lopez X. Karplus M. Gouverneur V. Tetrahedron  2001,  57:  10299 
    Suche in Google Scholar
  • Nickel:
  • 10d Horner L. Lindel H. Chem. Ber.  1985,  118:  676 
    Suche in Google Scholar
  • 11 Abrunhosa-Thomas I. Sellers CE. Montchamp J.-L. J. Org. Chem.  2007,  72:  2851 
    Suche in Google Scholar
12

Wilmad Glass Catalog No. 535-TR-7; www.wilmad-labglass.com.