Chemo-, Regio-, and Stereoselective Access to (E)-Boryl-Substituted Allyl Fluorides via Electrophilic Fluorodesilylation

Abstract

Here, we report a transition-metal-free chemo-, regio-, and stereoselective electrophilic fluorodesilylation of α-silyl-substituted allylboronate esters. The α-silyl-substituted allylboronate esters can be chemoselectively coupled with selectfluor resulting in a variety of (E)-boryl-substituted allyl fluorides in good yields with γ- and (E)-selectivity. The utilities of the obtained (E)-boryl-substituted allyl fluorides are highlighted by further modifications to afford allyl or alkyl fluoride derivatives.