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Volumn 64, Issue 22, 2008, Pages 5354-5361

Pd-catalyzed regioselective hydroarylation of α-(2-aminoaryl)-α,β-ynones with organoboron derivatives as a tool for the synthesis of quinolines: experimental evidence and quantum-chemical calculations

Author keywords

Alkynones; Boronic acids; DFT calculations; Hydroarylation; Palladium; Quinolines

Indexed keywords

1 [3 [2 (4 CHLOROPHENYL)QUINOLIN 4 YL]PHENYL]ETHANONE; 1 [3 [6,8 DIFLUORO 2(2 METHOXYPHENYL)QUINOLIN 4 YL]PHENYL]ETHANONE; 1 [4 [4 (1 NAPHTHYL)QUINOLIN 2 YL]PHENYL]ETHANONE; 2 (4 CHLOROPHENYL) 4 (4 FLUOROPHENYL)QUINOLINE; 2 (4 METHOXYPHENYL) 4 (1 NAPHTHYL)QUINOLINE; 2 (4 METHOXYPHENYL) 4 (4 METHYLPHENYL)QUINOLINE; 2 (4 TERT BUTYL CYCLOHEX 1 ENYL) 4 (4 METHYLSULFANYLPHENYL)QUINOLINE; 2 (4 TERT BUTYL CYCLOHEX 1 ENYL) 4 PHENYL QUINOLINE; 3 (2 AMINO 3,5 DIFLUOROPHENYL) 1 (2 METHOXYPHENYL)PROP 2 YN 1 ONE; 3 (2 AMINOPHENYL) 1 (2,4 DIMETHYLPHENYL)PROP 2 YN 1 ONE; 3 (2 AMINOPHENYL) 1 (4 TERT BUTYLCYCLOHEX 1 EN 1 YL)PROP 2 YN 1 ONE; 4 [3 [2 AMINO 4 (TRIFLUOROMETHYL)PHENYL]PROP 2 YNOYL]BENZONITRILE; 4 [4 (3 METHOXYPHENYL) 7 (TRIFLUOROMETHYL)QUINOLIN 2 YL]BENZONITRILE; 4 [4 (4 METHYLPHENYL) 7 (TRIFLUOROMETHYL)QUINOLIN 2 YL]BENZONITRILE; 4 [4 (METHYLTHIO)PHENYL] 2 (1 NAPHTHYL)QUINOLINE; KETONE DERIVATIVE; ORGANOBORON DERIVATIVE; PALLADIUM; QUINOLINE DERIVATIVE;

EID: 42749085676     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.03.015     Document Type: Article
Times cited : (67)

References (65)
  • 17
    • 42749089516 scopus 로고    scopus 로고
    • Selected references:
    • Selected references:
  • 52
    • 42749084624 scopus 로고    scopus 로고
    • note
    • 2/dppe, biphenyl (11 μmol) was detected by GLC analysis (24% yield based on the amount of Pd).
  • 62
    • 42749085178 scopus 로고    scopus 로고
    • note
    • It is important to remark that our PCM calculations, for which the knowledge of ethanol dielectric constant is necessary, were carried out at 298 K. Hence, our results can be only qualitatively extended at higher temperatures.
  • 64
    • 1642296152 scopus 로고    scopus 로고
    • 2-Ethynylaniline is commercially available (Aldrich). Substituted 2-ethynylanilines were obtained according to:
    • 2-Ethynylaniline is commercially available (Aldrich). Substituted 2-ethynylanilines were obtained according to:. Arcadi A., Bianchi G., and Marinelli F. Synthesis (2004) 610-618
    • (2004) Synthesis , pp. 610-618
    • Arcadi, A.1    Bianchi, G.2    Marinelli, F.3
  • 65
    • 42749083761 scopus 로고    scopus 로고
    • note
    • The reaction can be carried out also under a balloon of CO, with a slight decrease (≈10%) of yields.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.