Remote Deprotometalation-Iodolysis of N,N-Diisopropyl-2-trimethylsilylferrocenecarboxamide: A New Route Toward 1,1′-Disubstituted Ferrocenes

Lingaswamy Kadari (1, 2) , Thierry Roisnel (1) , William Erb (1) , Palakodety Radha Krishna (2) , Florence Mongin (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 IICT - CSIR Indian Institute of Chemical Technology [Hyderabad]

The 1,1′-disubstitution is currently the most frequent substitution pattern encountered in the ferrocene series. Here an original access based on the remote deprotometalation of N,N-diisopropyl-2-trimethylsilylferrocenecarboxamide is reported. The key intermediate, 1′-iodo-N,N-diisopropylferrocenecarboxamide, was prepared in multiple grams and was further functionalized toward fifteen 1′-substituted iodoferrocenes.

Mots clés: Ferrocene; 1; 1'; Disubstitution; Carboxamide; Remote functionalization; Functional group manipulation

Domaines: Chimie

Lingaswamy Kadari, Thierry Roisnel, William Erb, Palakodety Radha Krishna, Florence Mongin. Remote Deprotometalation-Iodolysis of N,N-Diisopropyl-2-trimethylsilylferrocenecarboxamide: A New Route Toward 1,1′-Disubstituted Ferrocenes. Synthesis: Journal of Synthetic Organic Chemistry, 2020, 52 (21), pp.3153-3161. ⟨10.1055/s-0040-1707175⟩. ⟨hal-02948487⟩