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Volumn 68, Issue 12, 2003, Pages 4918-4922

First regioselective ortho-lithiation induced by a 2-chloropyridyl group complexation

Author keywords

[No Author keywords available]

Indexed keywords

REGIOSELECTIVE ORTHO-LITHIATION;

EID: 0037602229     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026788g     Document Type: Article
Times cited : (34)

References (47)
  • 3
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    • and references therein
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    • (a) Mugesh, G.; Singh, H. B. Acc. Chem. Res. 2002, 35, 226. (b) Singh, H. B.; Sudha, N. J. Organomet. Chem. 1990, 397, 153. For a nonselective deprotonation of 2,2′-bipyridine and 2,4′-bipyridine with one nitrogen atom directing the lithiation, see: Zoltewicz, J. A.; Dill C. D. Tetrahedron 1996, 52, 14469.
    • (2002) Acc. Chem. Res. , vol.35 , pp. 226
    • Mugesh, G.1    Singh, H.B.2
  • 20
    • 0001703982 scopus 로고
    • (a) Mugesh, G.; Singh, H. B. Acc. Chem. Res. 2002, 35, 226. (b) Singh, H. B.; Sudha, N. J. Organomet. Chem. 1990, 397, 153. For a nonselective deprotonation of 2,2′-bipyridine and 2,4′-bipyridine with one nitrogen atom directing the lithiation, see: Zoltewicz, J. A.; Dill C. D. Tetrahedron 1996, 52, 14469.
    • (1990) J. Organomet. Chem. , vol.397 , pp. 153
    • Singh, H.B.1    Sudha, N.2
  • 21
    • 0030580395 scopus 로고    scopus 로고
    • (a) Mugesh, G.; Singh, H. B. Acc. Chem. Res. 2002, 35, 226. (b) Singh, H. B.; Sudha, N. J. Organomet. Chem. 1990, 397, 153. For a nonselective deprotonation of 2,2′-bipyridine and 2,4′-bipyridine with one nitrogen atom directing the lithiation, see: Zoltewicz, J. A.; Dill C. D. Tetrahedron 1996, 52, 14469.
    • (1996) Tetrahedron , vol.52 , pp. 14469
    • Zoltewicz, J.A.1    Dill, C.D.2
  • 26
    • 1542581810 scopus 로고
    • For reviews on N,P ligands and related metal complexes see: (a) Newkome, G. Chem. Rev. 1993, 93, 2067. (b) Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336.
    • (1993) Chem. Rev. , vol.93 , pp. 2067
    • Newkome, G.1
  • 27
    • 0033949478 scopus 로고    scopus 로고
    • For reviews on N,P ligands and related metal complexes see: (a) Newkome, G. Chem. Rev. 1993, 93, 2067. (b) Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336.
    • (2000) Acc. Chem. Res. , vol.33 , pp. 336
    • Helmchen, G.1    Pfaltz, A.2
  • 28
    • 0036774808 scopus 로고    scopus 로고
    • 2-Chloro-6-phenylpyridine (1) was prepared via a direct lithiation at the C-6 position of the 2-phenylpyridine with 3 equiv of the n-BuLi-LiDMAE superbase, see: Gros, Ph.; Fort, Y. Eur. J. Org. Chem. 2002, 3375.
    • (2002) Eur. J. Org. Chem. , pp. 3375
    • Gros, Ph.1    Fort, Y.2
  • 35
    • 0037782599 scopus 로고    scopus 로고
    • note
    • 1H spectroscopies.
  • 37
    • 0034655489 scopus 로고    scopus 로고
    • A nucleophilic substitution and a N-arylamination by Nickel clusters catalyzed by 1 afforded respectively compounds 5 and 6; see: (a) Desmarets, C.; Schneider, R.; Fort, Y. Tetrahedron Lett. 2000, 41, 2875. (b) Desmarets, C.; Schneider, R.; Fort, Y. Tetrahedron Lett. 2001, 42, 247. (c) Brenner, E.; Schneider, R.; Fort, Y. Tetrahedron Lett. 2000, 41, 2881. (d) Brenner, E.; Schneider, R.; Fort, Y. Tetrahedron 1999, 55, 12829.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 2875
    • Desmarets, C.1    Schneider, R.2    Fort, Y.3
  • 38
    • 0035825056 scopus 로고    scopus 로고
    • A nucleophilic substitution and a N-arylamination by Nickel clusters catalyzed by 1 afforded respectively compounds 5 and 6; see: (a) Desmarets, C.; Schneider, R.; Fort, Y. Tetrahedron Lett. 2000, 41, 2875. (b) Desmarets, C.; Schneider, R.; Fort, Y. Tetrahedron Lett. 2001, 42, 247. (c) Brenner, E.; Schneider, R.; Fort, Y. Tetrahedron Lett. 2000, 41, 2881. (d) Brenner, E.; Schneider, R.; Fort, Y. Tetrahedron 1999, 55, 12829.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 247
    • Desmarets, C.1    Schneider, R.2    Fort, Y.3
  • 39
    • 0034655783 scopus 로고    scopus 로고
    • A nucleophilic substitution and a N-arylamination by Nickel clusters catalyzed by 1 afforded respectively compounds 5 and 6; see: (a) Desmarets, C.; Schneider, R.; Fort, Y. Tetrahedron Lett. 2000, 41, 2875. (b) Desmarets, C.; Schneider, R.; Fort, Y. Tetrahedron Lett. 2001, 42, 247. (c) Brenner, E.; Schneider, R.; Fort, Y. Tetrahedron Lett. 2000, 41, 2881. (d) Brenner, E.; Schneider, R.; Fort, Y. Tetrahedron 1999, 55, 12829.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 2881
    • Brenner, E.1    Schneider, R.2    Fort, Y.3
  • 40
    • 0033615745 scopus 로고    scopus 로고
    • A nucleophilic substitution and a N-arylamination by Nickel clusters catalyzed by 1 afforded respectively compounds 5 and 6; see: (a) Desmarets, C.; Schneider, R.; Fort, Y. Tetrahedron Lett. 2000, 41, 2875. (b) Desmarets, C.; Schneider, R.; Fort, Y. Tetrahedron Lett. 2001, 42, 247. (c) Brenner, E.; Schneider, R.; Fort, Y. Tetrahedron Lett. 2000, 41, 2881. (d) Brenner, E.; Schneider, R.; Fort, Y. Tetrahedron 1999, 55, 12829.
    • (1999) Tetrahedron , vol.55 , pp. 12829
    • Brenner, E.1    Schneider, R.2    Fort, Y.3


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