Practical Chromatography-Free Synthesis of 2-Iodo-N,N-diiso­propylferrocenecarboxamide and Further Transformations

Abstract

An efficient procedure able to deliver grams of racemic and enantioenriched 2-iodo-N,N-diisopropylferrocenecarboxamide without chromatographic purification was developed. To introduce the halogen, two procedures, one using the nBuLi-TMEDA chelate and one using a lithium amide in the presence of ZnCl₂ as in situ trap were developed. Further functionalization by Suzuki–Miyaura and Ullman-type cross-couplings was investigated to access a variety of ferrocene derivatives.

Key words

ferrocene - carboxamide - large-scale synthesis - deprotometalation - Suzuki–Miyaura cross-coupling - Ullmann-type cross-coupling

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