Alkenylboronic Ester Activation to Nucleophilic Addition and Electrophilic Trapping with Carbonyl Groups

Carbolithiation of (1-phenylvinyl)boronic acid pinacol ester with tert-butyllithium was used to generate alpha-phenylboryl carbanions that reacted in a straightforward manner with carbonyl groups through a boron-Wittig sequence. When unhindered alpha, beta-unsaturated carbonyl compounds were used, 1,4-addition of the alpha-phenylboryl carbanions was observed over the boron-Wittig sequence.

Automated summary

In this study, the carbolithiation reaction was employed to generate alpha-phenylboryl carbanions, which then reacted with carbonyl compounds through a boron-Wittig sequence.