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Volumn 41, Issue 14, 2000, Pages 2377-2380

Silver salt-promoted direct cross-coupling reactions of alkynylsilanes with aryl iodides: Synthesis of aryl-substituted alkynylamides

Author keywords

Alkynes; Coupling reactions; Palladium catalyst; Silicon and compounds

Indexed keywords

ALKYNE; AMIDE; ORGANOMETALLIC COMPOUND; PALLADIUM; SILANE; SILICON DERIVATIVE;

EID: 0034175577     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00167-2     Document Type: Article
Times cited : (71)

References (28)
  • 1
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    • (a) Trost, B. M.; Fleming, I., Eds.; Pergamon Press: New York
    • (a) Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, pp. 521-549.
    • (1991) In Comprehensive Organic Synthesis , vol.3 , pp. 521-549
    • Sonogashira, K.1
  • 17
    • 0343665718 scopus 로고    scopus 로고
    • Preparation of alkynylsilanes 4: Treatment of 4-pentynamides with 2 equiv. of LDA followed by 2.5 equiv. of TMSCl afforded 4 in 93-95% yield
    • Preparation of alkynylsilanes 4: Treatment of 4-pentynamides with 2 equiv. of LDA followed by 2.5 equiv. of TMSCl afforded 4 in 93-95% yield.
  • 18
    • 0343665717 scopus 로고    scopus 로고
    • Note
    • 2S: C, 68.19, H; 5.72, N; 4.68. Found: C; 68.18, H; 5.95, N; 4.76.
  • 20
    • 0031004003 scopus 로고    scopus 로고
    • For Pd(0)-Cu(I)- or Pd(0)-catalyzed self-coupling of terminal alkynes, see: (a)
    • For Pd(0)-Cu(I)- or Pd(0)-catalyzed self-coupling of terminal alkynes, see: (a) Liu, Q.; Burton D. J. Tetrahedron Lett. 1997, 38, 4371-4374. (b) Vlassa, M.; Ciocan-Tarta, I.; Margineanu, F.; Oprean, I. Tetrahedron 1996, 52, 1337-1342. (c) Rossi, R.; Carpita, A.; Bigelli, C. Tetrahedron Lett. 1985, 26, 523-526.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 4371-4374
    • Liu, Q.1    Burton, D.J.2
  • 21
    • 0030033195 scopus 로고    scopus 로고
    • (b)
    • For Pd(0)-Cu(I)- or Pd(0)-catalyzed self-coupling of terminal alkynes, see: (a) Liu, Q.; Burton D. J. Tetrahedron Lett. 1997, 38, 4371-4374. (b) Vlassa, M.; Ciocan-Tarta, I.; Margineanu, F.; Oprean, I. Tetrahedron 1996, 52, 1337-1342. (c) Rossi, R.; Carpita, A.; Bigelli, C. Tetrahedron Lett. 1985, 26, 523-526.
    • (1996) Tetrahedron , vol.52 , pp. 1337-1342
    • Vlassa, M.1    Ciocan-Tarta, I.2    Margineanu, F.3    Oprean, I.4
  • 22
    • 0000175508 scopus 로고
    • (c)
    • For Pd(0)-Cu(I)- or Pd(0)-catalyzed self-coupling of terminal alkynes, see: (a) Liu, Q.; Burton D. J. Tetrahedron Lett. 1997, 38, 4371-4374. (b) Vlassa, M.; Ciocan-Tarta, I.; Margineanu, F.; Oprean, I. Tetrahedron 1996, 52, 1337-1342. (c) Rossi, R.; Carpita, A.; Bigelli, C. Tetrahedron Lett. 1985, 26, 523-526.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 523-526
    • Rossi, R.1    Carpita, A.2    Bigelli, C.3
  • 23
    • 0342360555 scopus 로고    scopus 로고
    • 2O has been reported, see: Ref. 16
    • 2O has been reported, see: Ref. 16.
  • 27
    • 0000098471 scopus 로고    scopus 로고
    • For information about recent advances in elucidating the mechanism of the related transmetallation between copper acetylides and palladium complexes; see
    • For information about recent advances in elucidating the mechanism of the related transmetallation between copper acetylides and palladium complexes; see: Osakada, K.; Sakata, R.; Yamamoto, T. Organometallics 1997, 16, 5354-5364.
    • (1997) Organometallics , vol.16 , pp. 5354-5364
    • Osakada, K.1    Sakata, R.2    Yamamoto, T.3
  • 28
    • 0342795483 scopus 로고    scopus 로고
    • Concerning cyclization of 7, see: Ref. 11. Detailed results for cyclization of other aryl-substituted alkynylamides 8-11 will appear in a full paper.
    • Concerning cyclization of 7, see: Ref. 11. Detailed results for cyclization of other aryl-substituted alkynylamides 8-11 will appear in a full paper.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.