Dehalogenative borylation of benzylic halides assisted by sodium dispersion

Abstract The reaction of benzyl chloride with isopropoxy-pinacolatoborane (iPrOBpin) in the presence of sodium dispersion (SD) afforded benzylboronate in a quantitative yield, in which the undesired dimerization of benzyl chloride was almost completely suppressed (<2%). The formation of related benzylic silane also proceeded with SD. Several benzylic halides were transformed into the corresponding boronates in a similar manner in up to 94% yield.