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Synthesis of Unsaturated Compounds

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Hydroboration and Organic Synthesis

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Abstract

As already mentioned, the internal triple bond is hydroborated (90–96%) with equimolar quantity of 9-BBN, while twofold excess of terminal alkyne is used for monohydroboration (90–100%) with 9-BBN [1]. Protonolysis of B-vinyl-9-BBN derivatives provides the corresponding alkenes. Thus, protonolysis of the product from 5-decyne and 9-BBN yields only cis-5-decene (Eq. 24.1).

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References

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(2007). Synthesis of Unsaturated Compounds. In: Hydroboration and Organic Synthesis. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-49076-0_24

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