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Mitchell, T.N.1
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66949180143
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note
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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.
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66949152576
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note
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4, and CsF failed to afford 2.
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21
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66949155421
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note
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Anhydrous MeCN and dioxane failed to afford 2.
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22
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0028334372
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These conditions are similar to the Heck conditions first described by Jefferey. See:
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These conditions are similar to the Heck conditions first described by Jefferey. See:. Jeffery T. Tetrahedron Lett. 35 (1994) 3051-3054
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(1994)
Tetrahedron Lett.
, vol.35
, pp. 3051-3054
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Jeffery, T.1
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24
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66949122242
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note
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Biaryl formation tracks with electrophile activation. For example, PhBr gave 1-2% biaryl, while biaryl production with 1-bromo-4-nitrobenzene exceeded 20%.
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25
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66949145182
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note
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2 ratio inhibited the reaction.
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26
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66949116775
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note
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4, filtered, and concentrated in vacuo. The product was purified by column chromatography on silica gel.
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31
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66949123930
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note
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Possible activation of the germanium by oxygen chelation:{A figure is presented}
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