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Volumn 65, Issue 16, 2009, Pages 3149-3154

A simple method for the direct arylation of indoles

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE;

EID: 61949486967     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.09.028     Document Type: Article
Times cited : (51)

References (41)
  • 16
    • 84980123932 scopus 로고
    • 2 arylated product, but not a 3,3-disubstituted indole. The presumed mechanism follows: initial deprotonation of indole, followed by arylation at C-3, and finally retro-Mannich to give the observed product. This work does not represent the first example of the direct arylation of an indole to give a C-3 quaternary center, rather, it was the 'presumed' intermediate that served as precedent for the reaction of bis-aryl iodide salts with indole derivatives. Our work is first to isolate and characterize C-3 quaternary indolines prepared by reaction of an indole and a bis-aryl iodide.
    • 2 arylated product, but not a 3,3-disubstituted indole. The presumed mechanism follows: initial deprotonation of indole, followed by arylation at C-3, and finally retro-Mannich to give the observed product. This work does not represent the first example of the direct arylation of an indole to give a C-3 quaternary center, rather, it was the 'presumed' intermediate that served as precedent for the reaction of bis-aryl iodide salts with indole derivatives. Our work is first to isolate and characterize C-3 quaternary indolines prepared by reaction of an indole and a bis-aryl iodide. Ebnöther A., Niklaus P., and Süess R. Helv. Chim. Acta (1969) 629-638
    • (1969) Helv. Chim. Acta , pp. 629-638
    • Ebnöther, A.1    Niklaus, P.2    Süess, R.3
  • 38
    • 0011668108 scopus 로고    scopus 로고
    • When unavailable commercially, bisacetoxy aryl iodides were prepared in one step according to Skulski's protocol: All boronic acids used are commercially available
    • When unavailable commercially, bisacetoxy aryl iodides were prepared in one step according to Skulski's protocol:. Kazmierczak P., Skulski L., and Kraszkiewicz L. Molecules 6 (2001) 881-891 All boronic acids used are commercially available
    • (2001) Molecules , vol.6 , pp. 881-891
    • Kazmierczak, P.1    Skulski, L.2    Kraszkiewicz, L.3
  • 39
    • 62049083902 scopus 로고    scopus 로고
    • note
    • As it pertains to the conversion from skatole to the unstable indolenine.
  • 40
    • 62049083738 scopus 로고    scopus 로고
    • note
    • 3-iodane.
  • 41
    • 62049085396 scopus 로고    scopus 로고
    • note
    • Reduction to the indoline is aided by the addition of silica gel.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.