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Synthesis 2023; 55(17): 2639-2647
DOI: 10.1055/a-2072-2754
DOI: 10.1055/a-2072-2754
short review
Reactions of Benzylboronate Nucleophiles
Financial support is acknowledged from the National Center for Research Resources (5P20RR016461) and the National Institute of General Medical Sciences (8P20GM103499) from the NIH. Additional support was provided to M.R.H. by the Howard Hughes Medical Institute to the College of Charleston as part of their 2012 Undergraduate Science Education Competition and to S.G.G. from an Organic Syntheses PUI grant. The NMR spectrometer at the College of Charleston was supported by the National Science Foundation under Grant No. 1429308.
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
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2072-2754.
- Supporting Information
Publication History
Received: 09 March 2023
Accepted after revision: 12 April 2023
Accepted Manuscript online:
12 April 2023
Article published online:
08 May 2023
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