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Synthesis 2010(9): 1505-1511
DOI: 10.1055/s-0029-1218691
DOI: 10.1055/s-0029-1218691
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkMild Conditions for Copper-Catalyzed N-Arylation of Imidazoles
Weitere Informationen
Received
7 December 2009
Publikationsdatum:
09. März 2010 (online)
Publikationsverlauf
Publikationsdatum:
09. März 2010 (online)

Abstract
An efficient copper(I) bromide catalyzed N-arylation of azoles with a variety of aromatic bromides and iodides under mild conditions is reported. This reaction displayed great functional group compatibility and excellent reactive selectivity.
Key words
copper - aryl halides - imidazoles - azoles - N-arylation
- For recent reviews, see:
- 1a
Wiglenda T.Ott I.Kircher B.Schumacher P.Schuster D.Langer T.Gust R. J. Med. Chem. 2005, 48: 6516MissingFormLabel - 1b
Jin Z. Nat. Prod. Rep. 2005, 22: 196MissingFormLabel - 1c
De Luca L. Curr. Med. Chem. 2006, 13: 1MissingFormLabel - 1d
Campeau L.-C.Fagnou K. Chem. Soc. Rev. 2007, 1058MissingFormLabel - 1e
Wiglenda T.Gust R. J. Med. Chem. 2007, 50: 1475MissingFormLabel - 1f
Kison C.Opatz T. Chem. Eur. J. 2009, 15: 843MissingFormLabel - 2a
Herrmann WA. Angew. Chem. Int. Ed. 2002, 41: 1290MissingFormLabel - 2b
Vargas VC.Rubio RJ.Hollis TK.Salcido ME. Org. Lett. 2003, 5: 4847MissingFormLabel - 2c
Perry MC.Cui X.Powell MT.Hou D.-R.Reibenspies JH.Burgess K. J. Am. Chem. Soc. 2003, 125: 113MissingFormLabel - 2d
Nair V.Bindu S.Sreekumar V. Angew. Chem. Int. Ed. 2004, 43: 5130MissingFormLabel - 2e
Enders D.Niemeier O.Henseler A. Chem. Rev. 2007, 107: 5606MissingFormLabel - Recent reviews on copper-catalyzed Ullmann reactions see:
- 3a
Hassan J.Sevignon M.Gozzi C.Schulz E.Lemaire M. Chem. Rev. 2002, 102: 1359MissingFormLabel - 3b
Kunz K.Scholz U.Ganzer D. Synlett 2003, 2428MissingFormLabel - 3c
Ley SV.Thomas AW. Angew. Chem. Int. Ed. 2003, 42: 5400MissingFormLabel - 3d
Beletskaya IP.Cheprakov AV. Coord. Chem. Rev. 2004, 248: 2337MissingFormLabel - 3e
Monnier F.Taillefer M. Angew. Chem. Int. Ed. 2008, 47: 3096MissingFormLabel - 3f
Evano G.Blanchard N.Toumi M. Chem. Rev. 2008, 108: 3054MissingFormLabel - 3g
Ma D.Cai Q. Acc. Chem. Res. 2008, 41: 1450MissingFormLabel - 3h
Monnier F.Taillefer M. Angew. Chem. Int. Ed. 2009, 48: 6954MissingFormLabel - 4
Lindley J. Tetrahedron 1984, 40: 1433 - 5a
Klapars A.Antilla JC.Huang X.Buchwald SL. J. Am. Chem. Soc. 2001, 123: 7727MissingFormLabel - 5b
Antilla JC.Klapars A.Buchwald SL. J. Am. Chem. Soc. 2002, 124: 11684MissingFormLabel - 5c
Antilla JC.Baskin JM.Barder TE.Buchwald SL. J. Org. Chem. 2004, 69: 5578MissingFormLabel - 5d
Altman RA.Buchwald SL. Org. Lett. 2006, 8: 2779MissingFormLabel - 5e
Altman RA.Koval ED.Buchwald SL. J. Org. Chem. 2007, 72: 6190MissingFormLabel - 5f
Jiang Q.Jiang D.Jiang Y.Fu H.Zhao Y. Synlett 2007, 1836MissingFormLabel - 5g
de Lange B.Lambers-Verstappen MH.de Vondervoort LS.Sereinig N.de Rijk R.de Vries AHM.de Vries JG. Synlett 2006, 3105MissingFormLabel - 5h
Cristau HJ.Cellier PP.Spindler JF.Taillefer M. Chem. Eur. J. 2004, 10: 5607MissingFormLabel - 5i
Zhang H.Cai Q.Ma D. J. Org. Chem. 2005, 70: 5164MissingFormLabel - 5j
Jerphagnon T.van Klink GPM.de Vries JG.van Koten G. Org. Lett. 2005, 7: 5241MissingFormLabel - 5k
Xie Y.-X.Pi S.-F.Wang J.Yin D.-L.Li J.-H. J. Org. Chem. 2006, 71: 8324MissingFormLabel - 5l
Liu L.Frohn M.Xi N.Dominguez C.Hungate R.Reider PJ. J. Org. Chem. 2005, 70: 10135MissingFormLabel - 5m
Zhu L.Cheng L.Zhang Y.Xie R.You J. J. Org. Chem. 2007, 72: 2737MissingFormLabel - 5n
Lv X.Bao W. J. Org. Chem. 2007, 72: 3863MissingFormLabel - 5o
Guo X.Rao H.Fu H.Jiang Y.Zhao Y. Adv. Synth. Catal. 2007, 348: 2197MissingFormLabel - 5p
Ma H.Jiang X. J. Org. Chem. 2007, 72: 8943MissingFormLabel - 5q
Cheng D.Gan F.Qian W.Bao W. Green Chem. 2008, 10: 171MissingFormLabel - 5r
Suresh P.Pitchumani K. J. Org. Chem. 2008, 73: 9121MissingFormLabel - 5s
Liang L.Li Z.Zhou X. Org. Lett. 2009, 11: 3294MissingFormLabel - 5t
Wang Y.Wu Z.Wang L.Li Z.Zhou X. Chem. Eur. J. 2009, 15: 8971MissingFormLabel - 5u
Xi Z.Liu F.Zhou Y.Chen W. Tetrahedron 2008, 64: 4254MissingFormLabel - 5v
Taillefer M.Xia N.Ouali A. Angew. Chem. Int. Ed. 2007, 46: 934MissingFormLabel - 5w
Bolm C.Correa A. Adv. Synth. Catal. 2007, 349: 2673MissingFormLabel - 5x
Wan J.Chai Y.Wu J.Pan Y. Synlett 2008, 3068MissingFormLabel - 5y
Bao W.Liu Y.Lv X. Synthesis 2008, 1911MissingFormLabel - 5z
Cheng C.Sun G.Wan J.Sun C. Synlett 2009, 2663MissingFormLabel - 6
Zhu L.Li G.Luo L.Guo P.Lan J.You J. J. Org. Chem. 2009, 74: 2200 - 7a
Wang D.Ding K. Chem. Commun. 2009, 1891MissingFormLabel - 7b
Wang D.Cai Q.Ding K. Adv. Synth. Catal. 2009, 351: 1722MissingFormLabel - 7c
Zhang Q.Wang D.Wang X.Ding K. J. Org. Chem. 2009, 74: 7187MissingFormLabel - 8a
Huang W.Shakespeare W. C. Synthesis 2007, 2121MissingFormLabel - 8b
Khan M. A.Polya J. B. Rev. Latinoam. Quim. 1972, 3: 119MissingFormLabel