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Volumn 9, Issue 12, 2011, Pages 4671-4684

N-aryl pyrazoles: DFT calculations of CH acidity and deprotonative metallation using a combination of lithium and zinc amides

Author keywords

[No Author keywords available]

Indexed keywords

ACIDITY; SUBSTRATES; ZINC COMPOUNDS;

EID: 79957981535     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c1ob05267e     Document Type: Article
Times cited : (52)

References (54)
  • 1
    • 0003607021 scopus 로고    scopus 로고
    • ed. A. R. Katritsky, C. W. Rees, E. F. V. Scriven), Pergamon, Elsevier Science Ltd., Oxford
    • J. Elguero, Comprehensive Heterocyclic Chemistry II (ed.:, A. R. Katritsky,,, C. W. Rees,,, E. F. V. Scriven,), Pergamon, Elsevier Science Ltd., Oxford, 1996, Vol. 3
    • (1996) Comprehensive Heterocyclic Chemistry II , vol.3
    • Elguero, J.1
  • 27
    • 77950595676 scopus 로고    scopus 로고
    • Major metallation at C5 and minor dimetallation at C5 and C2′ take place using butyllithium (see Ref. 3b). In contrast, metallation occurs regioselectively at C2′ employing ethylmagnesium bromide (see Ref. 3c)
    • Y. S. Halauko V. E. Matulis O. A. Ivashkevich Y. V. Grigoriev P. N. Gaponik Tetrahedron 2010 66 3415 3420
    • (2010) Tetrahedron , vol.66 , pp. 3415-3420
    • Halauko, Y.S.1    Matulis, V.E.2    Ivashkevich, O.A.3    Grigoriev, Y.V.4    Gaponik, P.N.5
  • 29
    • 70350137301 scopus 로고    scopus 로고
    • For a metallation similarly meta to a dimethylamino group, see:
    • B. Haag Z. Peng P. Knochel Org. Lett. 2009 11 4270 4273
    • (2009) Org. Lett. , vol.11 , pp. 4270-4273
    • Haag, B.1    Peng, Z.2    Knochel, P.3
  • 32
    • 65249111732 scopus 로고    scopus 로고
    • Concerning the ortho-directing power of fluorine, see:
    • M. Mosrin P. Knochel Org. Lett. 2009 11 1837 1840
    • (2009) Org. Lett. , vol.11 , pp. 1837-1840
    • Mosrin, M.1    Knochel, P.2
  • 35
    • 0033803029 scopus 로고    scopus 로고
    • Concerning the lithiation of 1,1′-(1,4-phenylene)bis(1H-pyrazole) (1i), see:
    • R. Mukherjee Coord. Chem. Rev. 2000 203 151 218
    • (2000) Coord. Chem. Rev. , vol.203 , pp. 151-218
    • Mukherjee, R.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.