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Please login to access the full content or check if you have access via2.11.8.8.3 Variation 3: Using Organozinc Reagents
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Negishi, E.-i.; Takahashi, T., Science of Synthesis, (2003) 2, 805.
It has been shown that the reaction of diethylzinc with 2 molar equivalents of an alk-1-ene, e.g. 147, in the presence of a catalytic amount of dichlorobis(η5-cyclopentadienyl)zirconium(IV) (49) and ethylmagnesium bromide in a ratio of 1:2, gives bis(2-ethylalkyl)zinc compounds, such as 471, in high yields. This reaction is generally significantly cleaner than the Dzhemilev ethylmagnesation (see Section 2.11.8.8.1). Furthermore, the organozinc products can directly undergo cross coupling in dimethylformamide with phenyl iodide, vinyl bromide, allyl bromide, and benzoyl chloride to give the corresponding cross-coupled products, e.g. 472, in good yields (Scheme 165).[195]
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References
[195] | Meeeeee, M.; Meeeeeeee, M. M.; Meeeeee, M., Meeeeeeeeeeeeee, (8888) 88, 8888. |
[387] | Meeeeee, M.; Meeeeeee, M. M., eeeeeeeeeee eeeeeee. |