- LiBr-Catalyzed C3-Disulfuration between Indole and N-Dithiophthalimide
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A simple, green halide-catalyzed protocol for disulfuration of indole derivatives with N-dithiophthalimides has been developed. This C-H disulfide reaction proceeded smoothly at room temperature with economical LiBr as catalyst, providing an effective method for the synthesis of novel unsymmetrical disulfides. A series of 3-dithioindole derivatives were obtained in high yields with good functional group tolerance; moreover, the wide scope of Harpp reagents (aryl, benzyl, primary, secondary, tertiary) confirmed the practicability of this approach.
- Li, Wangyu,Pan, Yuanjiang,Shi, Keqiang,Wang, Dungai
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- Steric and stereoscopic disulfide construction for cross-linkage via N -dithiophthalimides
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Disulfide bonds are a significant motif in life and drug-delivery systems. In particular, steric hindrance and stereoscopic disulfide linkers are closely associated with the stability of antibody-drug conjugates, which affects the potency, selectivity, and pharmacokinetics of drugs. However, limited availability and diversity of tertiary thiols impede the construction of steric and stereoscopic disulfides for cross-linkage in biochemistry and pharmaceuticals. Through modulating the mask effect of disulfurating reagents, we develop a facile and robust strategy for construction of diverse steric and stereoscopic disulfides via N-dithiophthalimides. The practical cross-linkage of biomolecules including amino acids, saccharides, and nucleosides with different drugs and fluorescent molecules is successfully established through hindered disulfide linkers.
- Gao, Wen-Chao,Jiang, Xuefeng,Shang, Yu-Zhu,Tian, Jun
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p. 3903 - 3908
(2020/04/27)
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