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Volumn 47, Issue 8, 2008, Pages 1503-1507

A general method for meta and para functionalization of arenes using TMP2Mg·2 LiCl

Author keywords

Arenes; Directed metalation; Grignard reagents; Magnesium bisamides; Phosphorodiamidates

Indexed keywords

ARENES; DIRECTED METALATION; GRIGNARD REAGENTS; MAGNESIUM BISAMIDES; PHOSPHORODIAMIDATES;

EID: 53249110866     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200703382     Document Type: Article
Times cited : (124)

References (68)
  • 42
    • 53549105209 scopus 로고    scopus 로고
    • For meta-metalation see: a P. C. Andrikopoulos, D. R. Armstrong, D. V. Graham, E. Hevia, A. R. Kennedy, R. E. Mulvey, C. T. O'Hara, C. Talmard, Angew. Chem. 2005, 117, 3525;
    • For meta-metalation see: a) P. C. Andrikopoulos, D. R. Armstrong, D. V. Graham, E. Hevia, A. R. Kennedy, R. E. Mulvey, C. T. O'Hara, C. Talmard, Angew. Chem. 2005, 117, 3525;
  • 52
    • 53549104694 scopus 로고    scopus 로고
    • Magnesiation of the phosphorodiamidate prepared from 3-bromophenol gave after iodolysis a mixture of 5-bromo-2-iodophenyl- (44% yield) and 3-bromo-2-iodophenyl-N,N,N′,N′-tetramethyldiamidophosphate (43% yield). For the 3-chlorophenol derivative, a mixture of 5-chloro-2-iodophenyl- (29% yield) and 3-chloro-2-iodophenyl-N,N,N′, N′-tetramethyldiamidophosphate (57% yield) was obtained. Moreover, metalation of the 3-fluorophenol derivative gave exclusively after iodolysis the 3-fluoro-2-iodophenyl-N,N,N′,N′-tetramethyldiamidophosphate in 73% yield (see the Supporting Information for details).
    • Magnesiation of the phosphorodiamidate prepared from 3-bromophenol gave after iodolysis a mixture of 5-bromo-2-iodophenyl- (44% yield) and 3-bromo-2-iodophenyl-N,N,N′,N′-tetramethyldiamidophosphate (43% yield). For the 3-chlorophenol derivative, a mixture of 5-chloro-2-iodophenyl- (29% yield) and 3-chloro-2-iodophenyl-N,N,N′, N′-tetramethyldiamidophosphate (57% yield) was obtained. Moreover, metalation of the 3-fluorophenol derivative gave exclusively after iodolysis the 3-fluoro-2-iodophenyl-N,N,N′,N′-tetramethyldiamidophosphate in 73% yield (see the Supporting Information for details).
  • 63
    • 31144432132 scopus 로고    scopus 로고
    • for a recent application of aryl nonaflates in palladium-catalyzed amination reactions see: d
    • for a recent application of aryl nonaflates in palladium-catalyzed amination reactions see: d) R. E. Tundel, K. W. Anderson, S. L. Buchwald, J. Org. Chem. 2006, 71, 430;
    • (2006) J. Org. Chem , vol.71 , pp. 430
    • Tundel, R.E.1    Anderson, K.W.2    Buchwald, S.L.3
  • 66
    • 34250314205 scopus 로고    scopus 로고
    • for a recent protocol for the reduction of aryl sulfonates see: b
    • for a recent protocol for the reduction of aryl sulfonates see: b) B. H. Lipshutz, B. A. Frieman, T. Butler, V. Kogan, Angew. Chem. 2006, 118, 814;
    • (2006) Angew. Chem , vol.118 , pp. 814
    • Lipshutz, B.H.1    Frieman, B.A.2    Butler, T.3    Kogan, V.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.