Work

Chemoselective Benzylation of Aldehydes Using Lewis Base Activated Boronate Nucleophiles

Year: 2018

Type: article

Abstract: 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 sec -butyl group, providing excellent yields of the benzylated products. 11 B NMR experiments were performed to study the mechanism of this transformation.

Source: Organometallics

DOI: 10.1021/acs.organomet.8b00085

Authors: Michael R. Hollerbach, Timothy J. Barker

Institution: College of Charleston

Language: English

Topic: Organoboron and organosilicon chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green