Synthesis, Inhaltsverzeichnis 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, USAFax: +1(504)2806860; e-Mail: snolan@uno.edu; Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik 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. Key words N-heterocyclic carbene - palladium - homogeneous catalysis Volltext Referenzen 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