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Volumn 6, Issue 20, 2004, Pages 3649-3652

Palladium-catalyzed cross-coupling reactions of 2-indolyldimethylsilanols with substituted aryl halides

Author keywords

[No Author keywords available]

Indexed keywords

HALIDE; PALLADIUM; SILANE DERIVATIVE;

EID: 6444228836     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048328a     Document Type: Article
Times cited : (68)

References (37)
  • 1
    • 0036798587 scopus 로고    scopus 로고
    • Recent reviews (a) Denmark, S. E.; Sweis, R. F. Acc. Chem. Res. 2002, 35, 835-845. (b) Denmark, S. E.; Sweis, R. F. Chem Pharm. Bull. 2002, 50, 1531-1541. (c) Denmark, S. E.; Ober, M. H. Aldrichimica Acta 2003, 36, 75-85.
    • (2002) Acc. Chem. Res. , vol.35 , pp. 835-845
    • Denmark, S.E.1    Sweis, R.F.2
  • 2
    • 1842843364 scopus 로고    scopus 로고
    • Recent reviews (a) Denmark, S. E.; Sweis, R. F. Acc. Chem. Res. 2002, 35, 835-845. (b) Denmark, S. E.; Sweis, R. F. Chem Pharm. Bull. 2002, 50, 1531-1541. (c) Denmark, S. E.; Ober, M. H. Aldrichimica Acta 2003, 36, 75-85.
    • (2002) Chem. Pharm. Bull. , vol.50 , pp. 1531-1541
    • Denmark, S.E.1    Sweis, R.F.2
  • 3
    • 1342311661 scopus 로고    scopus 로고
    • Recent reviews (a) Denmark, S. E.; Sweis, R. F. Acc. Chem. Res. 2002, 35, 835-845. (b) Denmark, S. E.; Sweis, R. F. Chem Pharm. Bull. 2002, 50, 1531-1541. (c) Denmark, S. E.; Ober, M. H. Aldrichimica Acta 2003, 36, 75-85.
    • (2003) Aldrichimica Acta , vol.36 , pp. 75-85
    • Denmark, S.E.1    Ober, M.H.2
  • 4
    • 6444243512 scopus 로고    scopus 로고
    • Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinhein, Chapter
    • (a) Hiyama, T., In Metal Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinhein, 1998; Chapter
    • (1998) Metal Catalyzed Cross-Coupling Reactions
    • Hiyama, T.1
  • 15
    • 0141919788 scopus 로고    scopus 로고
    • Reviews: (a) Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 1045-1075. (b) Gribble, G. W. Pure Appl. Chem. 2003, 75, 1417-1432.
    • (2003) Pure Appl. Chem. , vol.75 , pp. 1417-1432
    • Gribble, G.W.1
  • 19
    • 0032836483 scopus 로고    scopus 로고
    • (b) Ishikura and co-workers have demonstrated the cross-coupling of an in-situ-generated N-Boc(2-indolyl)boronate with aryl bromides from a 2-lithated indolyl species and triethylborane; see: Ishikura, M.; Agata, I.; Katagiri, N. J. Heterocycl. Chem. 1999, 36, 873-879.
    • (1999) J. Heterocycl. Chem. , vol.36 , pp. 873-879
    • Ishikura, M.1    Agata, I.2    Katagiri, N.3
  • 22
    • 6444242838 scopus 로고    scopus 로고
    • note
    • Preliminary experiments with KOTMS as the activator gave protiodesilylation as the major product, so we surmised that using KH as an activator would quickly and irreversibly deprotonate the silanol and remove the only available proton source as HT.
  • 35
    • 6444243513 scopus 로고    scopus 로고
    • note
    • Solubility in toluene (wt %) at 25°C: NaOt-Bu, 6%; KOt-Bu, 2.3%. LiOt-Bu is more soluble but less nucleophilic.
  • 36
    • 6444226571 scopus 로고    scopus 로고
    • note
    • Role of chloroform is currently unclear.
  • 37
    • 6444222932 scopus 로고    scopus 로고
    • note
    • Use of electron-rich phosphine ligands typically employed for the cross-coupling of aryl bromides failed with 1. 3653


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.