A benzylation of aldehydes using primary and secondary benzylboronic acid pinacol esters is reported. Activation of the boronic ester with s-butyllithium rendered it nucleophilic toward aldehydes. The activated nucleophile chemoselectively transfers the benzyl group over the s-butyl group, providing excellent yields of the benzylated products. 11B NMR experiments were performed to study the mechnism of this transformation.
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