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From 2-to 3-Substituted Ferrocene Carboxamides or How to Apply Halogen "Dance" to the Ferrocene Series

Abstract : Two methods were compared to convert ferrocene into N,N-diisopropylferrocenecarboxamide, N,N-diethylferrocenecarboxamide, N,N-dimethylferrocenecarboxamide, and (4-morphohnocarbonyl)ferrocene, namely, deprotometalation followed by trapping using dialkylcarbamoyl chlorides and amide formation from the intermediate carboxylic acid. The four ferrocene-carboxamides were functionalized at C-2; in the case of the less hindered and more sensitive amides, recourse to a mixed lithium-zinc 2,2,6,6-tetramethylpiperidino-based base allowed us to "achieve the reactions. Halogen migration using lithium amides was next optimized. Whereas it appeared impossible to isolate the less hindered 3-iodoferrocenecarboxamides, 3-iodo-N,N-diisopropylferrocenecarboxamide proved stable and was converted to new 1,3-disubstituted ferrocenes by Suzuki coupling or amide reduction. DFT calculations were used to rationalize the results obtained.
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Submitted on : Friday, April 20, 2018 - 11:57:11 AM
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Mehdi Tazi, William Erb, Yury S. Halauko, Oleg A. Ivashkevich, Vadim E. Matulis, et al.. From 2-to 3-Substituted Ferrocene Carboxamides or How to Apply Halogen "Dance" to the Ferrocene Series. Organometallics, American Chemical Society, 2017, 36 (24), pp.4770-4778. ⟨10.1021/acs.organomet.7b00659⟩. ⟨hal-01685699⟩

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