Synthesis 2006(15): 2475-2477  
DOI: 10.1055/s-2006-942471
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

Heck Cross-Coupling for Synthesizing Metal-Complexing Monomers

Glen E. Southard, Kelly A. Van Houten*, George M. Murray
Johns Hopkins University Applied Physics Laboratory, 11100 Johns Hopkins Road, Laurel, MD 20723-6099, USA
Fax: +1(443)7786914; e-Mail: Kelly.Van.Houten@jhuapl.edu;
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Publikationsverlauf

Received 6 February 2006
Publikationsdatum:
04. Juli 2006 (eFirst)

Abstract

New polymerizable ligands for complexing metal ions have been synthesized. The polymerizable ligands were made by Heck cross-coupling of aromatic bromides with high pressure ethylene gas under mild conditions at room temperature. The vinyl substituted ligands were prepared in good yields and characterized by GC-MS, FT-NMR, FT-IR and microanalysis.

    References

  • 1a Deluge M. Cai C. Langmuir  2005,  21:  1917 
  • 1b Calo V. Nacci A. Monopoli A. Ieva E. Cioffi N. Org. Lett.  2005,  7:  617 
  • 1c Arvela RK. Leadbeater NE. J. Org. Chem.  2005,  70:  1786 
  • 1d Mo J. Xu L. Xiao J. J. Am. Chem. Soc.  2005,  127:  751 
  • 1e Fristrup P. Le Quement S. Tanner D. Norrby P.-O. Organometallics  2004,  23:  6160 
  • 1f Chen C.-L. Liu Y.-H. Peng S.-M. Liu S.-T. Organometallics  2005,  24:  1075 
  • 1g Brenstrum T. Gerristma DA. Adjabeng GM. Frampton CS. Britten J. Robertson AJ. McNulty J. Capretta A. J. Org. Chem.  2004,  69:  7635 
  • 2a Knochel P. Singer RD. Chem. Rev.  1993,  93:  2117 
  • 2b Knochel P. Singer RD. Ber.  1997,  130:  1021 
  • 3a Gallagher WP. Maleczka RE. J. Org. Chem.  2005,  70:  841 
  • 3b Amatore C. Bahsoun AA. Jutand A. Meyer G. Ndedi Ntepe AN. Ricard L. J. Am. Chem. Soc.  2003,  125:  4212 
  • 4 Murray GM. Southard GE. In Molecular Imprinting: Science and Technology, Metal Ion Selective Molecularly Imprinted Materials   Yan M. Ramstrom O. Marcel Dekker; New York: 2004.  p.579-602  
  • 5 Shea KI. Stoddard GJ. Macromolecules  1991,  24:  1207 
  • 7 Southard GE. Murray GM. J. Org. Chem.  2005,  70:  9036 
  • 8a Littke AF. Fu GC. J. Am. Chem. Soc.  2001,  123:  6989 
  • 8b Littke AF. Fu GC. J. Org. Chem.  1999,  64:  10 
  • 8c Littke AF. Schwarz L. Fu GC. J. Am. Chem. Soc.  2002,  124:  6343 
  • 9 Lewis DF. Miller AM. Salvi GD. Inorg. Chem.  1995,  34:  3173 
  • 10 Beletskaya IP. Cheprakov AV. Chem. Rev.  2000,  100:  3009 ; and references therein
  • 11a Reddy KR. Surekha K. Lee GH. Peng SM. Liu ST. Organometallics  2000,  19:  2637 
  • 11b Detert H. Sugiono E. J. Prakt. Chem.  1999,  341:  358 
  • 12 Cornejo A. Fraile JM. Garcia JI. Garcia-Verdugo E. Gil MJ. Legarreta G. Luis SV. Martinez-Merino V. Mayoral JA. Org. Lett.  2002,  4:  3927 
  • 13 Hu Y.-Z. Zhang G. Thummel RP. Org. Lett.  2003,  5:  2251 
  • 14 Seidman M. Link K. J. Am. Chem. Soc.  1950,  72:  4324 
  • 15 Ramesh V. Umasundari P. Das KK. Spectrochim. Acta, Part A  1998,  54:  285 
  • 16 Wulff G. Akelah A. Makromol. Chem.  1979,  179:  2647 
6

4-Vinyl methylbenzoate was prepared in three steps starting with the bromination of 4-methyl methylbenzoate with NBS. The product, 4-bromomethyl methylbenzoate was converted to the phosphonium salt by reaction with triphenylphos-phine. Finally, 4-vinyl methylbenzoate was formed via Witting coupling of the corresponding phosphonium salt with formaldehyde.