1,1′-Bis-(n-benzotriazolyl) ferrocenecarboxamide: Precursor for synthesis of 1,1′-bis-ferrocenoyl esters and thioesters

•Novel 1,1′-bis-benzotriazolylferrocene was prepared for ferrocene functionalization.•Cheaper, easier and atom economic N-acylbenzotriazole method was used.•Microwave assisted chemistry have been used.

A microwave assisted synthesis methodology has been presented for the preparation of the bisferrocenoyl esters and thioesters. 1,1′-bis-ferrocenedicarboxylic acid was derivatized using direct 1H-benzotriazole/SOCl2 methodology to prepare 1,1′-bis-(N-benzotriazolyl) ferrocenecarboxamide, 1, as a convenient tool for the functionalization of ferrocene ring. The starting material, 1, was reacted with alcohols and thiols in mild conditions to prepare bisferrocenoyl esters and thioesters in high purity and in moderate yields. The solid state structure of 2b has also been determined by X-ray crystallography. H-bond interactions and plane geometries between ring systems have been discussed.

Graphical abstractSome 1,1′-bis ferrocene ester and thioester derivatives have been prepared using benzotriazole chemistry under microwave irradiation.Figure optionsDownload full-size imageDownload as PowerPoint slide