4.5 Article

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

Journal

SYNTHESIS-STUTTGART
Volume 52, Issue 21, Pages 3153-3161

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0040-1707175

Keywords

ferrocene; 1; 1 '-disubstitution; carboxamide; remote functionalization; functional group manipulation

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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 ofN,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.

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