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Functionalization of 3-Iodo-N,N-Diisopropylferrocene-Carboxamide, a Pivotal Substrate to Open the Chemical Space to 1,3-Disubstituted Ferrocenes

Abstract : From 2-iodo-N,N-diisopropylferrocenecarboxamide, the halogen 'dance' reaction was applied to deliver gram quantities of the 3-iodo isomer. The latter was successfully functionalized by Ullmann-type and Suzuki-Miyaura cross-couplings to build C-O and C-C bonds, respectively. Lithium/iodine exchange-electro-philic trapping sequences were also implemented to provide ferrocenes bearing valuable functional groups. Borane-mediated carboxamide reduction was next studied on selected substrates to deliver the corresponding amino derivatives in moderate to excellent yields. One of them, 1-(N,N-diisopropylaminomethyl)-3-iodoferrocene, was used as a substrate to access various iodoferrocene derivatives. Not only this work constitutes a general entry into the world of 1,3-disubstituted ferrocenes, but it also extends the chemical space available around this original scaffold.
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-02438541
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Submitted on : Wednesday, February 12, 2020 - 4:31:12 PM
Last modification on : Friday, July 10, 2020 - 4:00:46 PM
Long-term archiving on: : Wednesday, May 13, 2020 - 6:24:52 PM

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William Erb, Lingaswamy Kadari, Khadega Al-Mekhlafi, Thierry Roisnel, Vincent Dorcet, et al.. Functionalization of 3-Iodo-N,N-Diisopropylferrocene-Carboxamide, a Pivotal Substrate to Open the Chemical Space to 1,3-Disubstituted Ferrocenes. Advanced Synthesis and Catalysis, Wiley-VCH Verlag, 2020, 362 (4), pp.832-850. ⟨10.1002/adsc.201901393⟩. ⟨hal-02438541⟩

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