Alkylation and silylation of α-fluorobenzyl anion intermediates.

Org Biomol Chem

Division of Molecular Science, Graduate School of Science and Technology, 1-5-1, Tenjin-cho, Kiryu, Gunma 376-8515, Japan.

Published: November 2023

Simple α-fluorobenzyl anions reacted with electrophiles such as non-activated alkyl halides and chlorotrimethylsilane. Upon treatment with LTMP as the base, fluoromethylbenzenes took part in the formation of α-monofluorobenzyl anions without stabilizing -substituents. Furthermore, the resulting α-silyl fluoromethylbenzenes reacted with electrophiles such as acetophenone and benzaldehyde in the presence of cesium fluoride to form α-fluorobenzylated alcohols.

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http://dx.doi.org/10.1039/d3ob01586fDOI Listing

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