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Volumn 50, Issue 31, 2009, Pages 4407-4410

Reactions of vinyltributylgermanes and aryl halides under Heck conditions

Author keywords

Cross coupling; Heck reaction; Palladium; Vinylgermanes

Indexed keywords

ALKENYL GROUP; HALIDE; OXYGEN; PALLADIUM; VINYL DERIVATIVE;

EID: 66949135432     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.05.035     Document Type: Article
Times cited : (17)

References (31)
  • 16
  • 17
    • 66949180143 scopus 로고    scopus 로고
    • note
    • Faller and Kultyshev pointed out (Ref. 4a) the difficulty in assessing the extent to which, or even if, a Heck mechanism is operating during their chemistry. Under their conditions reaction of (E)-β-phenylethenylgermatrane with p-iodotoluene afforded the corresponding E-stilbene, whereas a 3.5/1 mixture of (Z/E)-β-phenylethenylgermatrane gave a 2.6/1 Z/E-mixture.
  • 20
    • 66949152576 scopus 로고    scopus 로고
    • note
    • 4, and CsF failed to afford 2.
  • 21
    • 66949155421 scopus 로고    scopus 로고
    • note
    • Anhydrous MeCN and dioxane failed to afford 2.
  • 22
    • 0028334372 scopus 로고
    • These conditions are similar to the Heck conditions first described by Jefferey. See:
    • These conditions are similar to the Heck conditions first described by Jefferey. See:. Jeffery T. Tetrahedron Lett. 35 (1994) 3051-3054
    • (1994) Tetrahedron Lett. , vol.35 , pp. 3051-3054
    • Jeffery, T.1
  • 23
  • 24
    • 66949122242 scopus 로고    scopus 로고
    • note
    • Biaryl formation tracks with electrophile activation. For example, PhBr gave 1-2% biaryl, while biaryl production with 1-bromo-4-nitrobenzene exceeded 20%.
  • 25
    • 66949145182 scopus 로고    scopus 로고
    • note
    • 2 ratio inhibited the reaction.
  • 26
    • 66949116775 scopus 로고    scopus 로고
    • note
    • 4, filtered, and concentrated in vacuo. The product was purified by column chromatography on silica gel.
  • 31
    • 66949123930 scopus 로고    scopus 로고
    • note
    • Possible activation of the germanium by oxygen chelation:{A figure is presented}


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.