Download PDF
Synthesis 2009(11): 1916-1922  
DOI: 10.1055/s-0028-1088060
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Convenient Methods for the Synthesis of a Library of Hemilabile Phosphines

M. Victoria Jiménez*, Jesús J. Pérez-Torrente, M. Isabel Bartolomé, Luis A. Oro
Departamento de Química Inorgánica, Instituto Universitario de Catálisis Homogénea-Instituto de Ciencia de Materiales de Aragón, Universidad de Zaragoza-C.S.I.C., 50009-Zaragoza, Spain
Fax: +34(976)762284; e-Mail: vjimenez@unizar.es;
Further Information

Publication History

Received 5 December 2008
Publication Date:
27 April 2009 (online)

    Permissions and Reprints All articles of this category

Abstract

A series of novel functionalized phosphines of hemi­labile character, R2P(CH2)nZ, have been prepared from diaryl­phosphines using several synthetic methodologies. The synthetic methods include the alkylation of lithium diarylphosphide or (di­arylphosphino)borane adducts with functionalized halogenoalkanes, X(CH2)nZ, and the photochemical hydrophosphination of suitable functionalized allyl or vinyl derivatives, H2C=CHZ or H2C=CHCH2Z, using white light. A range of R2PH (R = Bn, 4-MeOC6H4, 4-MeC6H4, 2-MeC6H4, Ph, 4-F3CC6H4) has been used in order to tune the electronic density on the phosphorus donor atom. The coordination ability of the hemilabile fragment was modified by selection of the donor group (Z = OMe, OEt, OBu, NMe2) or the length of the flexible carbon chain (n = 2, 3). Hemilabile fluorinated allylphosphines, R2PCH2CH=CH2 (R = 4-FC6H4, C6F5), have been prepared from diarylchlorophosphines and allylmagnesium bromide.

Key words

hemilabile ligands - functionalized phosphines - hydrophosphination - allylphosphine

    References

  • 1 Jeffrey JC. Rauchfuss TB. Inorg. Chem.  1979,  18:  2658 
    CrossrefGoogle Scholar
  • 2a Braunstein P. Naud F. Angew. Chem. Int. Ed.  2001,  40:  680 
    Google Scholar
  • 2b Slone CS. Weinberger DA. Mirkin CA. Prog. Inorg. Chem.  1999,  48:  233 
    Google Scholar
  • 3a Chen G. Lam WH. Fok WS. Lee HW. Kwong FY. Chem. Asian J.  2007,  2:  306 
    Google Scholar
  • 3b Chikkali S. Gudat D. Niemeyer M. Chem. Commun.  2007,  981 
    Google Scholar
  • 3c Grotjahn DB. Gong Y. Zakharov L. Golen JA. Rheingold AL. J. Am. Chem. Soc.  2006,  128:  438 
    Google Scholar
  • 3d Moxham GL. Randell-Sly HE. Brayshaw SK. Woodward RL. Weller AS. Willis MC. Angew. Chem. Int. Ed.  2006,  45:  7618 
    Google Scholar
  • 3e Braunstein P. Chem. Rev.  2006,  106:  134 
    Google Scholar
  • 4a Braunstein P. Knorr M. Stern C. Coord. Chem. Rev.  1998,  178-180:  903 
    Google Scholar
  • 4b Bader A. Lindner E. Coord. Chem. Rev.  1991,  108:  27 
    Google Scholar
  • 5 Espinet P. Soulantica K. Coord. Chem. Rev.  1999,  193-195:  499 
    CrossrefGoogle Scholar
  • 6a Jiménez MV. Pérez-Torrente JJ. Bartolomé MI. Gierz V. Lahoz FJ. Oro LA. Organometallics  2008,  27:  224 
    Google Scholar
  • 6b Jiménez MV. Rangel-Salas II. Lahoz FJ. Oro LA. Organometallics  2008,  27:  4229 
    Google Scholar
  • 7a McEwen WE. Smith JH. Woo EJ. J. Am. Chem. Soc.  1980,  102:  2746 
    Google Scholar
  • 7b McEwen WE. Janes AB. Knapczyk JW. Kyllingstad VL. Shiau WI. Shore S. Smith JH. J. Am. Chem. Soc.  1978,  100:  7304 
    Google Scholar
  • 8 Anderson GK. Kumar R. Inorg. Chem.  1984,  23:  4064 
    CrossrefGoogle Scholar
  • 9a Werner H. Hampp A. Windmüller B. J. Organomet. Chem.  1992,  435:  169 
    Google Scholar
  • 9b Werner H. Hampp A. Peters K. Peters EM. Walz L. von Schnering HG. Z. Naturforsch., B: Chem. Sci.  1990,  45:  1548 
    Google Scholar
  • 10 Unruh JD. Christenson JR. J. Mol. Catal.  1982,  14:  19 
    CrossrefGoogle Scholar
  • 11 Yamano M, Goto M, and Yamada M. inventors; EP  1,626,052. 
  • 12 Imamoto T. Kikuchi SI. Miura T. Wada Y. Org. Lett.  2001,  3:  87 
    CrossrefPubMedGoogle Scholar
  • 13 Brunel JM. Faure B. Maffei M. Coord. Chem. Rev.  1998,  178-180:  665 
    CrossrefGoogle Scholar
  • 14 Lebel H. Morin S. Paquet V. Org. Lett.  2003,  5:  2347 
    CrossrefPubMedGoogle Scholar
  • 15 McKinstry L. Livinghouse T. Tetrahedron  1995,  51:  7655 
    CrossrefGoogle Scholar
  • 16 Lindner E. Schmid M. Wegner P. Nachtigal C. Steimann M. Fawzi R. Inorg. Chim. Acta  1999,  296:  103 
    CrossrefGoogle Scholar
  • 17 Holmes-Smith RD. Osei RD. Stobart SR. J. Chem. Soc., Perkin Trans. 1  1983,  861 
    CrossrefGoogle Scholar
  • 18 Struck RF. Shealy YF. J. Med. Chem.  1966,  9:  414 
    CrossrefGoogle Scholar
  • 19a Thapper A. Sparr E. Jonson BFG. Lewis J. Raithby PR. Nordlander E. Inorg. Chem. Commun.  2004,  7:  443 
    Google Scholar
  • 19b Bassetti M. Alvarez P. Gimeno J. Lastra E. Organometallics  2004,  23:  5127 
    Google Scholar
  • 19c Barthel-Rosa LP. Maitra K. Nelson JH. Inorg. Chem.  1998,  37:  633 
    Google Scholar
  • 20 Ulmer L. Mattay J. Torres-García HG. Luftmann H. Eur. J. Mass Spectrom.  2000,  6:  49 
    CrossrefGoogle Scholar