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Synthesis 2010(6): 908-910
DOI: 10.1055/s-0029-1218643
DOI: 10.1055/s-0029-1218643
SHORTPAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkEfficient Copper-Catalyzed N-Arylation of Amides and Imidazoles with Aryl Iodides
Further Information
Received
22 October 2009
Publication Date:
08 January 2010 (online)
Publication History
Publication Date:
08 January 2010 (online)
Abstract
The C-N cross-coupling of amides and imidazoles with aryl iodides is described using CuI in tetrabutylammonium bromide (TBAB) under ligand-free conditions. The reaction is simple, general, and efficient affording the C-N cross-coupled products in shorter time and in high yield.
Key words
N-arylation - amides - imidazoles - copper iodide - TBAB
- Supporting Information for this article is available online:
- Supporting Information
- 1a
Ley SV.Thomas AW. Angew. Chem. Int. Ed. 2003, 42: 5400 ; Angew. Chem. 2003, 115, 5558 - 1b
Beletskaya IP.Cheprakov AV. Coord. Chem. Rev. 2004, 248: 2337 - 1c
Hartwig JF. Synlett 2006, 1283 - 1d
Corbet J.-P.Mignani G. Chem. Rev. 2006, 106: 2651 - 2a
Ullmann F. Ber. Dtsch. Chem. Ges. 1903, 36: 2382 - 2b
Goldberg I. Ber. Dtsch. Chem. Ges. 1906, 39: 1619 - For some examples with Pd catalysis, see:
- 3a
Ikawa T.Barder TE.Biscoe MR.Buchwald SL. J. Am. Chem. Soc. 2007, 129: 13001 - 3b
Yin J.Buchwald SL. J. Am. Chem. Soc. 2002, 124: 6043 - 3c
Huang X.Anderson KW.Zim D.Jiang L.Klapars A.Buchwald SL. J. Am. Chem. Soc. 2003, 125: 6653 - For some examples on Cu catalysis, see:
- 4a
Strieter ER.Blackmond DG.Buchwald SL. J. Am. Chem. Soc. 2005, 127: 4120 - 4b
Lv X.Bao W. J. Org. Chem. 2007, 72: 3863 - 4c
Hosseinzadeh R.Tajbakhsh M.Mohadjerani M.Mehdinejad H. Synlett 2004, 1517 - 4d
Guo X.Rao H.Fu H.Jiang Y.Zhao Y. Adv. Synth. Catal. 2006, 348: 2197 - 4e
Cristau H.-J.Cellier PP.Spindler J.-F.Taillefer M. Chem. Eur. J. 2004, 10: 5607 - 4f
Chen Y.-J.Chen H.-H. Org. Lett. 2006, 8: 5609 - 4g
Ma H.-C.Jiang X.-Z. J. Org. Chem. 2007, 72: 8943 - 4h
Yang M.Liu F. J. Org. Chem. 2007, 72: 8969 - 4i
Verma AK.Singh J.Sankar VK.Chaudhary R.Chandra R. Tetrahedron Lett. 2007, 48: 4207 - 4j
Rao H.Jin Y.Fu H.Jiang Y.Zhao Y. Chem. Eur. J. 2006, 12: 3636 - For Fe-catalyzed reactions, see:
- 5a
Correa A.Elmore S.Bolm C. Chem. Eur. J. 2008, 14: 3527 - 5b
Correa A.Bolm C. Angew. Chem. Int. Ed. 2007, 46: 8862 ; Angew. Chem. 2007, 119, 9018 - 6
Parvulescu VI.Hardacre C. Chem. Rev. 2007, 107: 2615 - For examples using TBAB as a reaction medium, see:
- 7a
Jammi S.Barua P.Rout P.Saha P.Punniyamurthy T. Tetrahedron Lett. 2008, 49: 1484 - 7b
Tang B.-X.Wang F.Li J.-H.Xie Y.-X.Zhang M.-B. J. Org. Chem. 2007, 72: 6294 - 7c
Calo V.Nacci A.Monopoli A.Laera S.Cioffi N. J. Org. Chem. 2003, 68: 2929 - For examples using TBAB as an additive, see:
- 8a
Li J.-H.Li J.-L.Wang D.-P.Pi S.-F.Xie Y.-X.Zhang M.-B.Hu X.-C. J. Org. Chem. 2007, 72: 2053 - 8b
Zhu X.Ma Y.Su L.Song H.Chen G.Liang D.Wan Y. Synthesis 2006, 3955 - 8c
Mino T.Shirae Y.Sasai Y.Sakamoto M.Fujita T. J. Org. Chem. 2006, 71: 6834 - 8d
Arvela RK.Leadbeater NE. Org. Lett. 2005, 7: 2101 - 8e
Schmink JR.Leadbeater NE. Org. Lett. 2009, 11: 2575 - 8f
Tagata T.Nishida M. J. Org. Chem. 2003, 68: 9412 - 8g
Alacid E.Najera C. J. Org. Chem. 2008, 73: 2315