High Reactivity of α-Boryl Radical of Potassium Alkyltrifluoroborate in Atom-Transfer Radical Addition.

We found that the α-boryl radical of potassium alkyltrifluoroborate shows higher reactivity compared to the α-boryl radicals of alkylboronic acid pinacol ester and alkyl N-methyl imidodiacetic acid (MIDA) boronate in the halogen atom abstraction step of atom-transfer radical addition (ATRA) between alkyl bromide and vinylborons. In this research, an ATRA of alkyl halides with potassium vinyltrifluoroborate furnished unique alkylborons, which are difficult to synthesize by other methods.