Nucleophilic fluoroalkylation of (bromomethyl)pinacolborane using silicon reagents

A method for the synthesis of pinacol boronic esters bearing a fluorinated group is described. •Nucleophilic fluoroalkylation of (bromomethyl)pincolborane.•Fluoroalkylation reactions using silicon reagents.•Intramolecular nucleophilic substitution. A method for the synthesis of pinacol boronic ester...

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Bibliographic Details
Published in:Journal of fluorine chemistry 2013-10, Vol.154, p.43-46
Main Authors: Levin, Vitalij V., Elkin, Pavel K., Struchkova, Marina I., Dilman, Alexander D.
Format: Article
Language:English
Subjects:
Bearing
Boranes
Borates
Esters
Fluorination
Nucleophilic fluoroalkylation
Organoboron compounds
Silanes
Silicon
Substitution
Synthesis
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Summary:A method for the synthesis of pinacol boronic esters bearing a fluorinated group is described. •Nucleophilic fluoroalkylation of (bromomethyl)pincolborane.•Fluoroalkylation reactions using silicon reagents.•Intramolecular nucleophilic substitution. A method for the synthesis of pinacol boronic esters bearing a fluorinated group at the α-carbon atom (RfCH2Bpin) from corresponding bromomethyl borane (BrCH2Bpin) and fluorinated silanes (RfSiMe3) is described. The fluoroalkylation reaction involves formation of borate anions followed by intramolecular nucleophilic substitution of bromine.
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2013.06.007