Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2008(14): 2221-2228
DOI: 10.1055/s-2008-1067147
DOI: 10.1055/s-2008-1067147
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Thiazole-Annelated Imidazolium Salts: A New Architecture for N-Heterocyclic Carbenes
Further Information
Received
5 May 2008
Publication Date:
18 June 2008 (online)
Publication History
Publication Date:
18 June 2008 (online)
Abstract
A short synthesis of thiazole-annelated imidazolium salts is presented. Deprotonation of these salts allowed the formation of new N-heterocyclic carbenes (NHCs) and the investigation of their respective electronic properties, which were determined by X-ray crystal structure analysis and IR spectroscopy of the corresponding iridium carbonyl complexes. Finally, the ability of these NHCs to form the corresponding palladium complexes was demonstrated.
Key words
N-heterocyclic carbene (NHC) - imidazolium salt - thiazole - NHC-metal complex
-
1a
Herrmann WA. Angew. Chem. Int. Ed. 2002, 41: 1290 -
1b
Kantchev EAB.O’Brien CJ.Organ MG. Angew. Chem. Int. Ed. 2007, 46: 2768 -
1c
N-Heterocyclic
carbenes in synthesis
Nolan SP. Wiley-VCH; Weinheim: 2006. -
1d
N-Heterocyclic
carbenes in transition metal catalysis
Glorius F. Springer; Berlin: 2007. - 2 For an excellent review on applications
in organocatalysis, see:
Enders D.Niemeier O.Henseler A. Chem. Rev. 2007, 107: 5606 - For an excellent overview on the variety of NHC structures and their coordination chemistry, see:
-
3a
Hahn FE.Jahnke MC. Angew. Chem. Int. Ed. 2008, 47: 3122 - See also:
-
3b
Scott NM.Nolan SP. Eur. J. Inorg. Chem. 2005, 1815 - For the design and application of the IBiox series of NHC ligands with different steric demand, see:
-
4a
Glorius F.Altenhoff G.Goddard R.Lehmann C. Chem. Commun. 2002, 2704 -
4b
Altenhoff G.Goddard R.Lehmann CW.Glorius F. Angew. Chem. Int. Ed. 2003, 42: 3690 -
4c
Altenhoff G.Goddard R.Lehmann CW.Glorius F. J. Am. Chem. Soc. 2004, 126: 15195 -
4d
Altenhoff G.Würtz S.Glorius F. Tetrahedron Lett. 2006, 47: 2925 -
5a
Burstein C.Lehmann CW.Glorius F. Tetrahedron 2005, 61: 6207 -
5b
Alcarazo M.Roseblade SJ.Cowley AR.Fernandez R.Brown JM.Lassaletta JM. J. Am. Chem. Soc. 2005, 127: 3290 - 6 For related NHCs, see:
Nonnenmacher M.Kunz D.Rominger F.Oeser T. Chem. Commun. 2006, 1378 ; and references cited therein - 7
Wong W.-Y.Chan S.-M.Choi K.-H.Cheah K.-W.Chan W.-K. Macromol. Rapid Commun. 2000, 21: 453 - CCDC 685503-685507 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk]. Data sets were collected with Nonius KappaCCD diffractometers, in the case of Mo-radiation equipped with a rotating anode generator. Programs used:
-
8a
COLLECT - data collection software: Nonius B. V., 1998
-
8b Data reduction Denzo-SMN:
Otwinowski Z.Minor W. Methods in Enzymology 1997, 276: 307 - For absorption correction SORTAV, see:
-
8c
Blessing RH. Acta Crystallogr. Sect. A 1995, 51: 33 -
8d
Blessing RH. J. Appl. Crystallogr. 1997, 30: 421 -
8e Denzo:
Otwinowski Z.Borek D.Majewski W.Minor W. Acta Crystallogr., Sect. A 2003, 59: 228 -
8f Structure solution SHELXS-97:
Sheldrick GM. Acta Crystallogr., Sect. A 1990, 46: 467 -
8g Structure refinement SHELXL-97:
Sheldrick GM. Acta Crystallogr., Sect. A 2008, 64: 112 -
8h Graphics SCHAKAL:
Keller E. Universität Freiburg 1997. - 9
Arduengo AJ. Acc. Chem. Res. 1999, 32: 913 - See for example:
-
10a
Magill AM.Cavell KJ.Yates BF. J. Am. Chem. Soc. 2004, 126: 8717 -
10b
Huang J.Schanz H.-J.Stevens ED.Nolan SP. Organometallics 1999, 18: 2370 -
10c
Luo L.Nolan SP. Organometallics 1994, 13: 4781 -
11a
Tolman CA. Chem. Rev. 1977, 77: 313 -
11b
Chianese AR.Li X.Janzen MC.Faller JW.Crabtree RH. Organometallics 2003, 22: 1663 -
11c
Chianese AR.Kovacevic A.Zeglis BM.Faller JW.Crabtree RH. Organometallics 2004, 23: 2461 -
11d
Kelly RA.Clavier H.Giudice S.Scott NM.Stevens ED.Bordner J.Samardjiev I.Hoff CD.Cavallo L.Nolan SP. Organometallics 2008, 27: 202 - 12 Additional reference data and a
pertinent discussion of NHC donor abilities can be found in the
supporting information of the following publication:
Fürstner A.Alcazaro M.Krause H.Lehmann CW. J. Am. Chem. Soc. 2007, 129: 12676 -
13a
Organ MG.Abdel-Hadi M.Avola S.Dubovyk I.Hadei N.Kantchev EAB.O’Brien CJ.Sayah M.Valente C. Chem. Eur. J. 2008, 14: 2443 -
13b
O’Brien CJ.Kantchev EAB.Valente C.Hadei N.Chass GA.Lough A.Hopkinson AC.Organ MG. Chem. Eur. J. 2006, 12: 4743 - 14
Katritzky AR.He H.-Y.Long Q.Cui X.Level J.Wilcox AL. ARKIVOC 2000, (iii): 240 - 15
Kennedy DF.Messerle BA.Smith MK. Eur. J. Inorg. Chem. 2007, 1: 80