Electrophilic aromatic substitution using fluorinated isoxazolines at the C5 position via C–F bond cleavage

Abstract

Electrophilic aromatic substitution at the C5 position of isoxazolines and construction of a new quaternary carbon center were achieved in this paper. This is the first report of carbon–carbon (C–C) bond formation onto isoxazoline without compromising the ring structure. Various aromatics including heteroaromatics gave the desired products in good yields, especially aromatics bearing electron-donating groups. The reaction proceeds via the S_EAr reaction mechanism, in which carbocation intermediates generated from the fluorinated isoxazolines via C–F bond cleavage reacted with aromatics.