Synthesis of Ferrocenyl Boranes and their Application as Lewis Acids in Epoxide Rearrangements

Abstract

A series of substituted ferrocenyl boron derivatives was synthesized. The oxidation of the ferrocenyl unit resulted in a significant increase of the boron-centered Lewis acidity. The neutral and cationic Lewis acids were characterized by NMR spectroscopy, crystal structure analysis and by computational methods. The new Lewis acids were then applied in the Meinwald rearrangement of epoxides, predominantly furnishing aldehydes as the kinetic products.