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Volumn 70, Issue 4, 2005, Pages 1501-1504

The first regioselective metalation and functionalization of unprotected 4-halobenzoic acids

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; CARBOXYLATION; CARBOXYLIC ACIDS; COMPLEXATION; FLUORINE COMPOUNDS; IODINE; NEGATIVE IONS;

EID: 13844315856     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0483365     Document Type: Article
Times cited : (26)

References (50)
  • 2
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    • Reviews: (b) Mortier, J.; Vaultier, M. In Recent Research Developments in Organic Chemistry; Transworld Research Network: Trivandrum, 1998; Vol. 2, p 269. (c) Mortier, J.; Vaultier, M. C. R. Acad. Sci. Série IIC 1998, 1, p 465.
    • (1998) Recent Research Developments in Organic Chemistry , vol.2 , pp. 269
    • Mortier, J.1    Vaultier, M.2
  • 3
    • 0032139454 scopus 로고    scopus 로고
    • Reviews: (b) Mortier, J.; Vaultier, M. In Recent Research Developments in Organic Chemistry; Transworld Research Network: Trivandrum, 1998; Vol. 2, p 269. (c) Mortier, J.; Vaultier, M. C. R. Acad. Sci. Série IIC 1998, 1, p 465.
    • (1998) C. R. Acad. Sci. Série IIC , vol.1 , pp. 465
    • Mortier, J.1    Vaultier, M.2
  • 9
    • 13844312162 scopus 로고    scopus 로고
    • Continuation-in-Part of co-pending U.S. Pat. 7850128, filed on March 12, 1992
    • Bennetau, B.; Cain, P. A. Continuation-in-Part of co-pending U.S. Pat. 7850128, filed on March 12, 1992.
    • Bennetau, B.1    Cain, P.A.2
  • 20
    • 13844312163 scopus 로고    scopus 로고
    • note
    • 3Et-1a-c were prepared in higher yield (respectively 57%, 60%, and 51%) by treatment of 3Me-1a-c with LTMP (3 equiv, -50°C/THF) followed by trapping with iodomethane.
  • 38
    • 0037033451 scopus 로고    scopus 로고
    • Polyiodinated pyrazines formed by treatment of fluoropyrazine with LTMP followed by quench with elemental iodine were reported to arise from an halogen-dance involving a iodine-lithium exchange reaction and not from a polylithiated intermediate: Toudic, F.; Plé, N.; Turck, A.; Quéguiner, G. Tetrahedron 2002, 58, 283.
    • (2002) Tetrahedron , vol.58 , pp. 283
    • Toudic, F.1    Plé, N.2    Turck, A.3    Quéguiner, G.4
  • 46
    • 0025021185 scopus 로고
    • 2 and esterification affords a symmetrical 1,9-diester. The initially formed 1-carboxylate is able to direct a second deprotonation of the 9-position during the quench. The intermediacy of a Quadac is clearly dependent on the nature of the electrophile and the substrate to be metalated. See: Palmer, B. D.; Boyd, M.; Denny, W. A. J. Org. Chem. 1990, 55, 438. (Chemical Equation Presented)
    • (1990) J. Org. Chem. , vol.55 , pp. 438
    • Palmer, B.D.1    Boyd, M.2    Denny, W.A.3
  • 47
    • 0034829342 scopus 로고    scopus 로고
    • Disilylation of aromatic compounds under basic conditions could be interpreted similarly: (a) Schlosser, M.; Guio, L.; Leroux, F. J. Am. Chem. Soc. 2001, 123, 3822.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 3822
    • Schlosser, M.1    Guio, L.2    Leroux, F.3
  • 48
    • 2142645600 scopus 로고
    • See also: (b) Taylor, R. Tetrahedron Lett. 1975, 16, 435. (c) Nwokogu, G. C.; Hart, H. Tetrahedron Lett. 1983, 24, 5725.
    • (1975) Tetrahedron Lett. , vol.16 , pp. 435
    • Taylor, R.1
  • 49
    • 0141490484 scopus 로고
    • See also: (b) Taylor, R. Tetrahedron Lett. 1975, 16, 435. (c) Nwokogu, G. C.; Hart, H. Tetrahedron Lett. 1983, 24, 5725.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 5725
    • Nwokogu, G.C.1    Hart, H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.