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Abstract The electrophilic cyclization via the boronate complex between various homoallylic boronates and Selectfluor® is reported. This reaction provides a fluoromethylated cyclopropane ring that was difficult to synthesize by previous methods. The use of phenyl lithium, which activates the homoallylic boronate, is important for the reaction. The intermediate boronate species in this reaction was observed through <sup>11</sup>B NMR experiments.
The first catalytic intermolecular 1,2-alkylborylation reaction via a radical-relay mechanism between unactivated olefins, bis(pinacolato)diboron, and an alkyl electrophile is reported. Successful implementation of this method requires that the competing boryl substitution of the alkyl electrophile is retarded to facilitate the radical relay.
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