Direct C–H alkoxylation of BODIPY dyes <i>via</i> cation radical accelerated oxidative nucleophilic hydrogen substitution: a new route to building blocks for functionalized BODIPYs
Heng Li, Fan Lv, Xing Guo, Qinghua Wu, Hao Wu, Bing Tang, Changjiang Yu, Hua Wang, Lijuan Jiao, Erhong Hao
Abstract
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.