Direct sulfonylation of BODIPY dyes with sodium sulfinates through oxidative radical hydrogen substitution at the α-position,Chemical Communications

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Direct sulfonylation of BODIPY dyes with sodium sulfinates through oxidative radical hydrogen substitution at the α-position
Chemical Communications ( IF 4.3 ) Pub Date : 2020-11-19 , DOI: 10.1039/d0cc07259a
Fan Lv _{1,

2,

3,

4,

5} , Xing Guo _{1,

2,

3,

4,

5} , Hao Wu _{1,

2,

3,

4,

5} , Heng Li _{1,

2,

3,

4,

5} , Bing Tang _{1,

2,

3,

4,

5} , Changjiang Yu _{1,

2,

3,

4,

5} , Erhong Hao _{1,

2,

3,

4,

5} , Lijuan Jiao _{1,

2,

3,

4,

5}

Affiliation

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.

中文翻译：

BODIPY染料与亚磺酸钠的直接磺酰化反应是通过在α位上的氧化自由基进行氢取代

首次描述了通过自由基方法将BODIPY染料与亚磺酸钠直接磺酰化的有效便捷方法。该转化呈现出宽的底物范围和高的区域选择性，提供了一系列α-磺酰化的BODIPY。有意义的是，磺酰基作为良好的离去基团，可以在BODIPY核心上轻松引入各种功能。此外，一个2,4-二硝基苯磺酰基（DBS）基团取代的BODIPY通过光致电子转移（PET）途径显示出急剧淬灭的荧光，并被证明是用于选择性生物硫醇检测的新型荧光探针。

更新日期：2020-11-27

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