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Please login to access the full content or check if you have access via7.6.11.4 Method 4: Coupling Reactions Using Catalytic Nickel(II) Chloride and Buta-1,3-diene
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Takahashi, T.; Liu, Y., Science of Synthesis, (2004) 7, 603.
As described in Section 7.6.11.1, a major problem in the cross coupling of alkyl Grignard reagents with alkyl halides is β-hydride elimination from alkyl halides after oxidative addition and the role of the alkyl Grignard as a hydrogen source. In order to avoid both of these problems, the addition of buta-1,3-dienes has been found to be very effective. For example, if 1-bromodecane is treated with butylmagnesium chloride in the presence of 1 mol% nickel(II) chloride and 10 mol% buta-1,3-diene at 0°C for 30 minutes, the cross-coupling product tetradecane (18) is formed in 100% yield (Scheme 13). This reaction does not proceed with aryl bromides. Therefore, when both aryl bromide and alkyl bromide functionalities are present in one molecule, only the alkyl bromide moiety reacts with excellent chemoselectivity.[2–4]
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References
| [2] | Meeee, M.; Meeeeeee, M.; Meeee, M.; Meeeeeee, M.; Meeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [3] | Meeee, M.; Meeee, M.; Meeeeeee, M.; Meeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [4] | Máeeeeee, M. M., Meeee. Meee., (8888) 888, 888; Meeee. Meee. Mee. Me., (8888) 88, 888. |
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- 8.Meeeee-Meee, (8888) M 88-8, 888.
- 8.Meeeee-Meee, (8888) M 88e, 8888.
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