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

Organic & Biomolecular Chemistry Pub Date: 2021-05-11 DOI: 10.1039/D1OB00376C

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.

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