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铑(III)催化的 C-H 活化/环化反应合成吖啶鎓和荧蒽鎓盐:细胞器特异性线粒体染色应用。

Rh(iii)-Catalysed synthesis of cinnolinium and fluoranthenium salts using C-H activation/annulation reactions: organelle specific mitochondrial staining applications.

机构信息

Organic & Bioorganic Chemistry Laboratory, CSIR-Central Leather Research Institute, Adyar, Chennai-600020, India.

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.

出版信息

Org Biomol Chem. 2021 Jun 28;19(24):5413-5425. doi: 10.1039/d1ob00376c. Epub 2021 May 28.

Abstract

The construction of a novel class of indazolo[2,1-a]cinnolin-7-ium and diazabenzofluoranthenium salts was developed by using Rh(iii)-catalyzed C-H activation/annulation reactions with 2-phenyl-2H-indazole, and internal alkynes, which resulted in structurally important polycyclic heteroaromatic compounds (PHAs). This reaction uses mild reaction conditions and has a high efficiency, low catalyst loading, and wide substrate scope. The overall catalytic process involves C-H activation followed by C-C/C-N bond formation. Furthermore, the synthesised cinnolinium/fluoranthenium salts exhibit potential fluorescence properties and 5i was targeted in particular for specific mitochondrial staining in order to investigate cancer cell lines.

摘要

新型吲哚并[2,1-a]咔啉-7-鎓和二氮杂苯并芴𬭩盐的构建是通过 Rh(iii)催化的 C-H 活化/环化反应,以 2-苯基-2H-吲哚和内炔为原料,得到结构重要的多环杂芳烃(PHA)。该反应使用温和的反应条件,具有高效率、低催化剂负载和广泛的底物范围。整个催化过程涉及 C-H 活化,然后是 C-C/C-N 键形成。此外,合成的咔啉鎓/芴𬭩盐表现出潜在的荧光性质,特别是 5i 被靶向用于特定的线粒体染色,以研究癌细胞系。

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