Reactions of Benzylboronate Nucleophiles

Abstract This short review summarizes our laboratory’s development of benzylboronic esters as nucleophiles. Activation of the benzylboronic ester is achieved by irreversible coordination of an alkyllithium Lewis base to form a nucleophilic benzylboronate. This boronate was found to react with aldehydes, imines, ketones, and alkyl bromides. A copper catalyst was employed in reactions of the boronate with epoxides and aziridines. 1 Introduction 2 1,2-Additions 3 Additions to sp3 Electrophiles 4 Conclusion and Outlook