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Updated: Nov 30, 2025

Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology
Published on: March 12, 2015
Synthesis of Chiral-Substituted 2-Aryl-ferrocenes by the Catellani Reaction
Raviraj Ananda Thorat1, Saket Jain1, Moh Sattar1
1Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhopal Bypass Road, Bhauri, Bhopal, Madhya Pradesh 462066, India.
Abstract:
A palladium-catalyzed and norbornene-mediated methodology has been developed for the synthesis of chiral 2-aryl-ferroceneamides from chiral 2-iodo-N,N-diisopropylferrocencarboxamide, iodoarenes, and alkenes using a JohnPhos ligand and potassium carbonate as a base in dimethylformamide at 105 °C. The developed three-component coupling protocol allows the compatibility of electron-withdrawing fluoro, chloro, ester, and nitro and electron-donating methyl, methoxy, dimethoxy, benzyl ether-substituted iodo-benzenes, other iodoarenes, such as iodo-naphthalene, heteroarenes, such as iodothiophene, and terminating substrates, such as methyl, ethyl, tert-butyl acrylates, and substituted styrenes with 2-iodo-N,N-diisopropylferrocencarboxamide. Furthermore, the developed three-component Catellani method proceeded with the retention of the configuration of the planar chiral ferrocene, which depends on the role of the participating carbon-iodine bond in ferrocene. Consequently, the developed protocol enabled the formation of densely substituted chiral 2-aryl ferroceneamides, exhibiting good to excellent enantioselectivity. The conversion of an ester of the synthesized chiral 2-aryl ferroceneamides has also been carried out to further accommodate the easily expendable acid and alcohol functionalities.
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