Reactions of Benzylboronate Nucleophiles

Timothy J. Barker; Andrew Bogatkevich; Dallas W. Crowder; Sophia G. Gierszal; Jacob C. Hayes; Michael R. Hollerbach; Richard W. Russell

doi:10.1055/a-2072-2754

Synthesis, Table of Contents

Synthesis 2023; 55(17): 2639-2647
DOI: 10.1055/a-2072-2754

short review

Reactions of Benzylboronate Nucleophiles

Authors

Timothy J. Barker∗
Andrew Bogatkevich
Dallas W. Crowder
Sophia G. Gierszal
Jacob C. Hayes
Michael R. Hollerbach
Richard W. Russell

Abstract

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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

Key words

boron - benzylation - Lewis base - copper - boronate

Full Text

References

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