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

William Erb (1) , Thierry Roisnel (1) , Vincent Dorcet (1)

1 ISCR - Institut des Sciences Chimiques de Rennes

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 n BuLi-TMEDA chelate and one using a lithium amide in the presence of ZnCl (2) 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.

Keywords: Suzuki-Miyaura cross-coupling; Ullmann-type cross-coupling; deprotometalation; large-scale synthesis; carboxamide; Ferrocene; large scale synthesis

Domains: Chemical Sciences; Coordination chemistry

William Erb, Thierry Roisnel, Vincent Dorcet. Practical Chromatography-Free Synthesis of 2-Iodo-N,N-diisopropylferrocenecarboxamide and Further Transformations. Synthesis: Journal of Synthetic Organic Chemistry, 2019, 51 (17), pp.3205-3213. ⟨10.1055/s-0039-1689917⟩. ⟨hal-02303395⟩