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Volumn 125, Issue 40, 2003, Pages 12084-12085

Synthesis of substituted oxindoles from α-chloroacetanilides via palladium-catalyzed C - H functionalization

Author keywords

[No Author keywords available]

Indexed keywords

ACETANILIDE DERIVATIVE; ALPHA CHLOROACETANILIDE DERIVATIVE; CARBON; HYDROGEN; OXINDOLE; OXINDOLE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

EID: 0141923586     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja037546g     Document Type: Article
Times cited : (363)

References (33)
  • 2
    • 0003979828 scopus 로고    scopus 로고
    • Academic Press: London
    • Sundberg, R. J. Indoles; Academic Press: London, 1996; pp 17, 152-154.
    • (1996) Indoles , pp. 17
    • Sundberg, R.J.1
  • 18
    • 0141916281 scopus 로고    scopus 로고
    • See Supporting Information
    • See Supporting Information.
  • 19
    • 0141881756 scopus 로고    scopus 로고
    • note
    • Higher catalyst loadings are required to achieve complete conversion for these substrates, likely due to nonproductive, competitive oxidative addition at the aryl chloride, Thus, bromide or iodide substituents on the aromatic ring are presumably not compatible with our current protocol.
  • 26
    • 0000210279 scopus 로고
    • Another possibility is that rotation about the carbonyl C-N bond of the palladium enolate into a reactive conformation is slow relative to the palladation event. For an analogous situation, see: Cohen, T.; McMullen, C. H.; Smith, K. J. Am. Chem. Soc. 1968, 90, 6866. We are grateful to a reviewer for making this suggestion.
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 6866
    • Cohen, T.1    McMullen, C.H.2    Smith, K.3
  • 28
    • 0037936773 scopus 로고    scopus 로고
    • This mechanistic dichotomy has been discussed previously. See (a) Sezen, B.; Sames, D. J. Am. Chem. Soc. 2003. 125, 5274.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 5274
    • Sezen, B.1    Sames, D.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.