RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2006(2): 366-367
DOI: 10.1055/s-2005-918497
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
Weitere Informationen
Received
26 September 2005
Publikationsdatum:
21. Dezember 2005 (online)
Publikationsverlauf
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.
Key words
N-heterocyclic carbene - palladium - homogeneous catalysis
-
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 MethodsRicci 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