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Volumn 8, Issue 11, 2007, Pages 1561-1566

Selective arylation of 2-substituted indoles towards 1,2- and 2,3-functional indoles directed through the catalytic system

Author keywords

C Arylation; N Arylation; Palladium; Substituted indoles

Indexed keywords

FUNCTIONAL ANALYSIS; PALLADIUM; SYNTHESIS (CHEMICAL); TUNING;

EID: 34548699867     PISSN: 15667367     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.catcom.2007.01.009     Document Type: Article
Times cited : (23)

References (48)
  • 1
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    • Academic Press, London
    • Sundberg R.J. Indoles (1996), Academic Press, London
    • (1996) Indoles
    • Sundberg, R.J.1
  • 2
    • 0010653530 scopus 로고    scopus 로고
    • Thomas E.J. (Ed), Thieme, Stuttgart
    • Joule J.A. In: Thomas E.J. (Ed). Science of Synthesis 10 (2001), Thieme, Stuttgart 361
    • (2001) Science of Synthesis , vol.10 , pp. 361
    • Joule, J.A.1
  • 3
    • 0001319053 scopus 로고
    • Katritzky A.R., and Rees C.W. (Eds), Pergamon, Oxford
    • Sundberg R.J. In: Katritzky A.R., and Rees C.W. (Eds). Comprehensive Heterocyclic Chemistry 4 (1984), Pergamon, Oxford 314
    • (1984) Comprehensive Heterocyclic Chemistry , vol.4 , pp. 314
    • Sundberg, R.J.1
  • 44
    • 33646152128 scopus 로고    scopus 로고
    • Recently Echavarren and co-workers reported a computational study that support a Pd(II)/Pd(IV) catalytic cycle for palladium catalysed domino reactions involving aryl iodides as substrates. See:
    • Recently Echavarren and co-workers reported a computational study that support a Pd(II)/Pd(IV) catalytic cycle for palladium catalysed domino reactions involving aryl iodides as substrates. See:. Cardenas D.J., Martin-Matute B., and Echavarren A.M. J. Am. Chem. Soc. 128 (2006) 5033
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 5033
    • Cardenas, D.J.1    Martin-Matute, B.2    Echavarren, A.M.3
  • 45
    • 34548697018 scopus 로고    scopus 로고
    • note
    • The products obtained in those cases correspond to the free carboxylic acids. The arylation reaction results probably from the reaction between the 2-(methyl-carboxylate)indole and the aryl halide as the free carboxylic acid did not gave the expected compound. The ester functionality is most likely saponified under the basic reaction conditions used in these experiments.
  • 46
    • 34548689802 scopus 로고    scopus 로고
    • note
    • Extended MM2 parameters, extended to transition metals by the user, implemented in CAChe (Futjitsu) version 6.1 was used for calculation.
  • 48
    • 34548688346 scopus 로고    scopus 로고
    • note
    • Independently of the reactions conditions, reacting 2-phenylindole with phenylbromide or phenyliodide gave almost exclusively the homocoupling product (i.e. biphenyl >90% yield).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.