Direct sulfonylation of BODIPY dyes with sodium sulfinates through oxidative radical hydrogen substitution at the α-position
Fan Lv, Xing Guo, Hao Wu, Heng Li, Bing Tang, Changjiang Yu, Erhong Hao, Lijuan Jiao
Abstract
An efficient and convenient protocol for the direct sulfonylation of BODIPY dyes with sodium sulfinates via a radical process is described for the first time. This transformation presented wide substrate scope and high regioselectivity, providing a series of α-sulfonylated BODIPYs. Meaningfully, the sulfonyl group, as a good leaving group, allowed the facile introduction of a variety of functionalities on the BODIPY core. Moreover, a 2,4-dinitrobenzenesulfonyl (DBS) group substituted BODIPY showed dramatically quenched fluorescence via the photoinduced electron transfer (PET) pathway, and was demonstrated as a new fluorescent probe for selective biothiol detection.