Synthesis of novel ferrocene labelled steroidal derivatives via palladium-catalysed carbonylation. X-ray structure of 17-(N-(4′-((2-ferrocenyl-ethenyl)-carbonyl)-phenyl)carbamoyl)-5α-androst-16-ene

Homogeneous catalytic carbonylation of some representative steroidal substrates (alkenyl iodides/enol triflates 1–5) has been carried out in the presence of (E)-1-(4′-aminophenyl)-3-ferrocenyl-prop-2-en-1-one (6) as the nucleophile. The products 1a–4a were obtained in moderate to good yield (43–75%) and were characterised with various spectroscopic methods (1H-, 13C NMR, IR, MS).The solid state structure of 17-(N-(4′-((2-ferrocenyl-ethenyl)-carbonyl)-phenyl)-carbamoyl)-5α-androst-16-ene (1a) has also been determined by X-ray crystallography.

Graphical abstractPalladium-catalysed aminocarbonylation of steroidal alkenyl iodides has been carried out in the presence of ferrocenyl chalcone 6. The products were obtained in moderate to good yield and were characterised with various spectroscopic methods. The solid state structure of 17-(N-(4′-((2-ferrocenyl-ethenyl)-carbonyl)-phenyl)-carbamoyl)-5α-androst-16-ene (1a) has been determined by X-ray crystallography.Figure optionsDownload full-size imageDownload as PowerPoint slide