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Volumn 46, Issue 15, 2005, Pages 2563-2566

Phosphine-catalyzed regioselective heteroaromatization between activated alkynes and isocyanides leading to pyrroles

Author keywords

Activated alkyne; Heteroaromatization; Isocyanide; Organocatalyst; Phosphine catalyzed reaction; Pyrrole; 3+2 Cycloaddition

Indexed keywords

ALKYNE DERIVATIVE; CYANIDE; ISOCYANIC ACID DERIVATIVE; PHOSPHINE; PYRROLE DERIVATIVE;

EID: 15244343667     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.02.104     Document Type: Article
Times cited : (45)

References (23)
  • 1
    • 0035886887 scopus 로고    scopus 로고
    • Reviews on the organocatalyzed reactions, see: P.I. Dalko, and L. Moisan Angew. Chem., Int. Ed. 40 2001 3726 3748 and references cited therein
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 3726-3748
    • Dalko, P.I.1    Moisan, L.2
  • 3
    • 0034867881 scopus 로고    scopus 로고
    • Review on the phosphine-catalyzed reactions: X. Lu, C. Zhang, and Z. Xu Acc. Chem. Res. 34 2001 535 544 and references cited therein
    • (2001) Acc. Chem. Res. , vol.34 , pp. 535-544
    • Lu, X.1    Zhang, C.2    Xu, Z.3
  • 6
    • 0001492474 scopus 로고    scopus 로고
    • G. Maas Georg Thieme Stuttgart
    • D.S. Black G. Maas Science of Synthesis Vol. 9 2001 Georg Thieme Stuttgart 441 552
    • (2001) Science of Synthesis , vol.9 , pp. 441-552
    • Black, D.S.1
  • 9
    • 0001563584 scopus 로고
    • The reactions using dppp as an organocatalyst: B.M. Trost, and C.-J. Li J. Am. Chem. Soc. 116 1994 10819 10820
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 10819-10820
    • Trost, B.M.1    Li, C.-J.2
  • 11
    • 85030817345 scopus 로고    scopus 로고
    • note
    • +) 225.099. Found: 225.099
  • 12
    • 85030807003 scopus 로고    scopus 로고
    • note
    • The CuCl catalyst probably coordinates both dppp and the isocyanide in this case. The coordination to the isocyanide makes it easy to generate the anionic intermediate 2′ in Scheme 2 and stabilizes the derived species. Moreover, the ligation to the phosphine holds intermediates B and 2′ close together and accelerates the formation of the cyclized intermediate C
  • 18
    • 85030812769 scopus 로고    scopus 로고
    • See Ref. 2
    • See Ref. 2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.