- Di(isopropylprenyl)borane: A new hydroboration reagent for the synthesis of alkyl and alkenyl boronic acids
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The best of the old: The new hydroboration reagent 1 combines the selectivity of disiamylborane (2) with the reactivity towards carbonyls of allyl boranes 3. Conventional oxidative workup conditions are avoided, as facile hydrolysis in protic media provides the corresponding boronic acids with up to 99% anti-Markovnikov selectivities. A one-pot hydroboration/ Suzuki-Miyaura protocol adds to the synthetic value of 1.
- Kalinin, Alexey V.,Scherer, Stefan,Snieckus, Victor
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p. 3399 - 3404
(2007/10/03)
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- Process for preparing bisallylboranes and nonaromatic boronic acids
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A process for preparing bisallylboranes of the formula (I) by reacting a diene with sodium borohydride in the presence of an oxidant in an inert solvent, with the borane generated in situ reacting selectively with the diene to form the bis(allyl)borane of the formula (I) and the substituents R1 to R6 having the following meanings: R1-R6 are H, aryl or substituted or unsubstituted C1-C4-alkyl or two radicals R may be closed to form a cyclic system. As oxidant, it is possible to use, for example, alkyl halides or dialkyl sulfates. In a particularly preferred embodiment, the diene used is 2,5-dimethylhexa-2,4-diene (R1, R2, R5, R6=methyl, R3, R4=H).
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