Direct C-H alkoxylation of BODIPY dyes via cation radical accelerated oxidative nucleophilic hydrogen substitution: a new route to building blocks for functionalized BODIPYs.

Oxidative nucleophilic α-hydrogen substitution is a direct method for BODIPY functionalization. However, it was hampered by the low reactivity of BODIPYs toward weak nucleophiles. Herein, we develop a cation radical accelerated oxidative nucleophilic α-hydrogen substitution reaction between BODIPY dyes and a variety of alcohols. This direct C-H alkoxylation presented a wide substrate scope and high site selectivity, providing a series of α-alkoxylated BODIPYs with diverse functional groups. Moreover, a BODIPY derivative with a pyridinium ion was developed as a new mitochondria-targeting fluorescent probe with favorable photophysical properties.