Synthesis 2006(2): 366-367  
DOI: 10.1055/s-2005-918497
PSP
© Georg Thieme Verlag Stuttgart · New York

Large-Scale One-Pot Synthesis of N-Heterocyclic Carbene-Pd(allyl)Cl Complexes

Oscar Navarro, Steven P. Nolan*
Department of Chemistry, University of New Orleans, New Orleans, LA 70148, USA
Fax: +1(504)2806860; e-Mail: snolan@uno.edu;
Weitere Informationen

Publikationsverlauf

Received 26 September 2005
Publikationsdatum:
21. Dezember 2005 (online)

Abstract

Improved one-pot syntheses of (IPr)Pd(allyl)Cl {IPr = [N,N′-bis(2,6-diisopropylphenyl)imidazol]-2-ylidene} and (SIPr)Pd(allyl)Cl {SIPr = [N,N′-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol]-2-ylidene} complexes are described. This simple method utilizes technical grade isopropanol and water as solvents, affording gram quantities of the cross-coupling pre-catalysts.

    References

  • 1a Arduengo AJ. Rasika Dias HV. Harlow RL. Kine M. J. Am. Chem. Soc.  1992,  114:  5530 
  • For reviews on NHC, see:
  • 1b Regitz M. Angew. Chem., Int. Ed. Engl.  1996,  35:  725 
  • 1c Arduengo AJ. Krafczyk R. Chem. Unserer Zeit  1998,  32:  6 
  • For reviews, see:
  • 2a Scott NM. Nolan SP. Eur. J. Inorg. Chem.  2005,  1815 
  • 2b Herrmann WA. Angew. Chem. Int. Ed.  2002,  41:  1290 
  • 3 Jafarpour L. Nolan SP. Adv. Organomet. Chem.  2001,  46:  181 ; P(t-Bu)3 was not included in this study
  • 4 Collman JP. Hedegus LS. Norton JR. Finke RG. Principles and Applications of Organotransition Metal Chemistry   2nd ed.:  University Science; Mill Valley, CA: 1987. 
  • 5 Viciu MS. Germaneau RF. Navarro-Fernandez O. Stevens ED. Nolan SP. Organometallics  2002,  21:  5470 
  • 6 Viciu MS. Navarro O. Germaneau RF. Kelly RA. Sommer W. Marion N. Stevens ED. Cavallo L. Nolan SP. Organometallics  2004,  23:  1629 
  • 7 Miyaura N. Top. Curr. Chem.  2002,  219:  11 
  • 8a Navarro O. Kaur H. Mahjoor P. Nolan SP. J. Org. Chem.  2004,  69:  3173 
  • 8b Navarro O. Oonishi Y. Kelly RA. Stevens ED. Briel O. Nolan SP. J. Organomet. Chem.  2004,  689:  3722 
  • 8c

    Navarro, O.; Mei, J.; Stevens, E. D.; Scott, N. M.; Viciu, M. S.; Nolan, S. P. submitted for publication.

  • 9 Hartwig JF. Modern Amination Methods   Ricci A. Wiley-VCH; Weinheim: 2000. 
  • 10 Culkin DA. Hartwig JF. Acc. Chem. Res.  2003,  36:  234 
  • 11 Viciu MS. Germaneau RF. Nolan SP. Org. Lett.  2002,  4:  4053 
  • 12 Jackstell R. Harkal S. Jiao Ha. Spannenberg A. Borgmann C. Roettger D. Nierlich F. Elliot M. Niven S. Cavell K. Navarro O. Viciu MS. Nolan SP. Beller M. Chem.-Eur. J.  2004,  10:  3891 
  • 13 Jensen DR. Sigman MS. Org. Lett.  2003,  5:  63 
  • 14 Viciu MS. Zinn FK. Stevens ED. Nolan SP. Organometallics  2003,  22:  3175 
  • (IPr)Pd(allyl)Cl is commercially available from Strem Chemicals in small quantities (hundreds of mg) and from Umicore AG in larger quantities. For more references on uses of this pre-catalyst, see:
  • 15a Marion N. Navarro O. Kelly RA. Nolan SP. Synthesis  2003,  2590 
  • 15b Scott NM. Navarro O. Briel O. Nolan SP. Chem. Today  2005,  23:  25 
  • 16 IPr·HCl and SIPr·HCl are commercially available from Strem Chemicals