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Volumn , Issue 19, 2008, Pages 3041-3045

Sila-sonogashira cross-coupling reactions of activated aryl chlorides with alkynylsilanes

Author keywords

Alkynyl silane; Aryl chloride; Copper; Diarylethynes; Palladium; Sonogashira reaction

Indexed keywords

1 PHENYL 2 (4 ACETYLPHENYL)ETHYNE; 1 PHENYL 2 TRIMETHYLSILYLETHYNE; 4 ACETYLPHENYL CHORIDE; 4 NITROPHENYL CHLORIDE; ACETYLENE DERIVATIVE; CHLORIDE; COPPER; PALLADIUM; UNCLASSIFIED DRUG;

EID: 57649134973     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0028-1087345     Document Type: Article
Times cited : (38)

References (87)
  • 4
    • 0036643463 scopus 로고    scopus 로고
    • For examples of recent reviews, see: (a) Sonogashira, K. J. Organomet. Chem. 2002, 653, 46
    • For examples of recent reviews, see: (a) Sonogashira, K. J. Organomet. Chem. 2002, 653, 46.
  • 41
    • 0037149925 scopus 로고    scopus 로고
    • and references therein, (b) Eberhard, M. R.; Wang, Z.; Jensen, C. M. Chem. Commun. 2002, 818.
    • and references therein, (b) Eberhard, M. R.; Wang, Z.; Jensen, C. M. Chem. Commun. 2002, 818.
  • 77
    • 0000187088 scopus 로고    scopus 로고
    • The copper-free version of sila-Sonogashira cross-coupling reaction has been achieved using a palladium/imidazolium salt system, see: (a) Yang, C, Nolan, S. P. Organometallics 2002, 21, 1020
    • The copper-free version of sila-Sonogashira cross-coupling reaction has been achieved using a palladium/imidazolium salt system, see: (a) Yang, C.; Nolan, S. P. Organometallics 2002, 21, 1020.
  • 79
    • 0037136485 scopus 로고    scopus 로고
    • For examples of modified sila-Sonogashira cross-coupling reaction under basic conditions, see: (a) Mio, M. J, Kopel, L. C, Braun, J. B, Gadzikwa, T. L, Hull, K. L, Brisbois, R. G, Markworth, C. J, Grieco, P. A. Org. Lett. 2002, 4, 3199
    • For examples of modified sila-Sonogashira cross-coupling reaction under basic conditions, see: (a) Mio, M. J.; Kopel, L. C.; Braun, J. B.; Gadzikwa, T. L.; Hull, K. L.; Brisbois, R. G.; Markworth, C. J.; Grieco, P. A. Org. Lett. 2002, 4, 3199.
  • 83
    • 0347985383 scopus 로고    scopus 로고
    • The presence of the copper(I) cocatalyst inhibited product formation, see: Gelman, D.; Buchwald, S. L. Angew. Chem. Int. Ed. 2003, 42, 5993.
    • The presence of the copper(I) cocatalyst inhibited product formation, see: Gelman, D.; Buchwald, S. L. Angew. Chem. Int. Ed. 2003, 42, 5993.
  • 87
    • 57649128629 scopus 로고    scopus 로고
    • Typical Procedure for the Sila-Sonogashira Cross-Coupling Reactions of Aryl Chlorides 2 with Alkynylsilanes 1 To a solution of Pd(OAc)2 (45 mg, 0.2 mmol, 10 mol, and, )-DIOP (100 mg, 0.2 mmol, 10 mol, in dry DMF (8 mL) were added 1-(4-methoxypheny)-2-trimethylsilylethyne (1b, 519 μL, 2.4 mmol, 4-cyanophenyl chloride (2b, 275 mg, 2 mmol, and CuCl (20 mg, 0.2 mmol, 10 mol, at r.t. The dark red suspension was heated for 12 h at 120°C and monitored by GC and TLC. After completion of the reaction, the reaction mixture was quenched with 1 M HCl and extracted with Et2O (3 x 20 mL, The combined organics were washed with brine and dried over anhydrous MgSO4. Filtration and concentration with a rotary evaporator gave a viscous oil. The residue was purified by flash column chromatography on SiO 2 (hexane-Et2O, 8:2, Rf, 0.39, 3h 331 mg, 1.42 mmol, 71, was obtained as a white solid
    • 3): δ = 3.84 (s, 3 H), 6.89-6.92 (m, 2 H), 7.47-7.50 (m, 2 H), 7.56-7.64 (m, 4 H).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.