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Base‐Promoted Regioselective Synthesis of α‐Amino BODIPYs through Cross‐Dehydrogenative Coupling with Anilines
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2024-06-29 , DOI: 10.1002/ejoc.202400660
Hua Wang 1 , Luying Guo 1 , Huiquan Zuo 1 , Long Wang 1 , Xing Guo 1 , Zhengxin Kang 1 , Zhong-Yuan Li 1 , Lijuan Jiao 2 , Erhong Hao 3
Affiliation  

The construction of C‐N bond at the α‐position of BODIPYs (boron dipyrromethene) not only enables flexible reactivity but also leads to strong electron‐donating properties. In this study, a base‐promoted oxidative cross‐dehydrogenative coupling was developed to synthesize α‐amino BODIPYs with air as a green oxidant. By this strategy, a series of weak nitrogen nucleophiles, such as heteroaryl and aryl anilines, were installed to the α‐position. Remarkably, pyrrole, pyrazole and indole were also employed to realize the synthesis of α‐heteroaryl BODIPYs through direct functionalization. Further aggregation‐induced emission enhancement (AIE) properties and lipid droplet‐targeting bioimaging experiments of representative dyes demonstrated their potential applications as organic probes.

中文翻译:


通过苯胺交叉脱氢偶联碱促进区域选择性合成 α-氨基 BODIPY



BODIPY(二吡咯亚甲基硼)α位上的C-N键结构不仅能够实现灵活的反应性,而且具有很强的给电子特性。在这项研究中,开发了一种碱促进的氧化交叉脱氢偶联方法,以空气作为绿色氧化剂合成α-氨基BODIPY。通过这种策略,一系列弱氮亲核试剂,例如杂芳基和芳基苯胺,被安装到α位。值得注意的是,吡咯、吡唑和吲哚也被用来通过直接官能化实现α-杂芳基BODIPY的合成。代表性染料的进一步聚集诱导发射增强(AIE)特性和脂滴靶向生物成像实验证明了它们作为有机探针的潜在应用。
更新日期:2024-06-29
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