Synthesis of unsymmetrical multi-aroyl derivatives of ferrocene using palladium catalysed oxidative C–H aroylation

Abstract

A palladium catalysed methodology for mono-selective oxidative aroylation of ferrocene has been achieved. 10 mol% of Pd(OAc)₂ was used as the catalyst for this radical aroylation reaction using O-methyl-oxime as the directing group. tert-Butyl hydroperoxide was used as an oxidant and both aldehydes and alcohols were used as acyl-equivalents. The protocol has been extended to aryl, heteroaryl and sterically hindered aroylating agents. Acidic-hydrolysis with 6(N) HCl of the directing group resulted in unsymmetrically substituted ketone derivatives of ferrocene, which have not been achieved otherwise.