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Synlett 2011(7): 1038-1042
DOI: 10.1055/s-0030-1259729
DOI: 10.1055/s-0030-1259729
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Copper-Catalyzed Aromatic C-H Bond Halogenation Using Lithium Halides as Halogenating Reagents
Weitere Informationen
Received
30 November 2010
Publikationsdatum:
10. März 2011 (online)
Publikationsverlauf
Publikationsdatum:
10. März 2011 (online)
Abstract
The copper-catalyzed C-H halogenation of 2-arylpyridines containing a variety of electron-withdrawing and electron-donating substituents was described. It is worth noting that cheap and easy-to-handle lithium halides were utilized as the halogen sources.
Key words
copper - C-H activation - halogenation - lithium halide - arylpyridines
- Supporting Information for this article is available online:
- Supporting Information
- Primary data for this article are available online and can be cited using the following DOI: 10.4125/pd0009th:
- Primary Data MS data and associated files for the ¹H and ¹³C NMR spectra for the compounds 3a-o are summarized.
- For reviews, see:
-
1a
Dyker G. Angew. Chem. Int. Ed. 1999, 38: 1698 -
1b
Ritleng V.Sirlin C.Pfeffer M. Chem. Rev. 2002, 102: 1731 ; and references cited therein -
1c
Giri R.Shi B.-F.Engle KM.Maugel N.Yu J.-Q. Chem. Soc. Rev. 2009, 38: 3242 -
1d
Lyons TW.Sanford MS. Chem. Rev. 2010, 110: 1147 -
1e
Bellina F.Rossi R. Chem. Rev. 2010, 110: 1082 -
1f
Colby DA.Bergman RG.Ellman JA. Chem. Rev. 2010, 110: 624 - For representative examples of the copper-catalyzed C-C bond formation, see:
-
2a
Tang BX.Song RJ.Wu CY.Liu Y.Zhou MB.Wei WT.Deng GB.Yin DL.Li JH. J. Am. Chem. Soc. 2010, 132: 8900 -
2b
Mousseau JJ.Bull JA.Charette AB. Angew. Chem. Int. Ed. 2010, 49: 1115 -
2c
Do HQ.Daugulis O. Org. Lett. 2010, 12: 2517 -
2d
Kawano T.Matsuyama N.Hirano K.Satoh T.Miura M. J. Org. Chem. 2010, 75: 1764 -
2e
Yotphan S.Bergman RG.Ellman JA. Org. Lett. 2009, 11: 1511 -
2f
Li C.-J. Acc. Chem. Res. 2009, 42: 335 - For representative examples of the copper-catalyzed C-heteroatom bond formation, see:
-
3a
Kawano T.Hirano K.Satoh T.Miura M. J. Am. Chem. Soc. 2010, 132: 6900 -
3b
Zhang LN.Ang GY.Chiba S. Org. Lett. 2010, 12: 3682 -
3c
Bernini R.Fabrizi G.Sferrazza A.Cacchi S. Angew. Chem. Int. Ed. 2009, 48: 8078 -
3d
Wang WH.Luo F.Zhang SH.Cheng J. J. Org. Chem. 2010, 75: 2415 -
3e
King AE.Huffman LM.Casitas A.Costas M.Ribas X.Stahl SS. J. Am. Chem. Soc. 2010, 132: 12068 -
4a
Ullmann’s Encyclopedia of Industrial
Chemistry
6th ed.:
Wiley-VCH;
Weinheim:
2002.
-
4b
Davos SG. Organotransition Metal Chemistry: Application to Organic Synthesis Pergamon Press; Oxford: 1982. -
5a
Sasson Y. In The Chemistry of Functional Group: The Chemistry of Halides, Pseudo-halides and Azides Part 1, Suppl. D2:Patai S.Rappoport Z. John Wiley and Sons; Chichester: 1995. -
5b
de la Mare PDB. Electrophilic Halogenation Cambridge University Press; New York: 1976. - 6
Wan XB.Ma ZX.Li BJ.Zhang KY.Cao SK.Zhang SW.Shi ZJ. J. Am. Chem. Soc. 2006, 128: 7416 - 7
Kalyani D.Dick AR.Anani WQ.Sanford MS. Org. Lett. 2006, 8: 2523 -
8a
Song BR.Zheng XJ.Mo J.Xu B. Adv. Synth. Catal. 2010, 352: 329 -
8b
Zheng XJ.Song BR.Li GF.Liu BX.Deng HM.Xu B. Tetrahedron Lett. 2010, 51: 6641 - 9
Mei T.-S.Giri R.Maugel N.Yu J.-Q. Angew. Chem. Int. Ed. 2008, 47: 5215 - 10
Chen X.Hao XS.Goodhue CE.Yu J.-Q. J. Am. Chem. Soc. 2006, 128: 6790 -
11a
Yang LJ.Lu Z.Stahl SS. Chem. Commun. 2009, 6460 -
11b
Menini L.Gusevskaya EV. Chem. Commun. 2006, 209 -
11c
Menini L.Parreira LA.Gusevskaya EV. Tetrahedron Lett. 2007, 48: 6401 - 12
Barnes JC.Hume DN. Inorg. Chem. 1963, 2: 444