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The facile dearomatization of nitroaromatic compounds using lithium enolates of unsaturated ketones in conjugate additions and (4+2) formal cycloadditions

Abstract : The dearomatization of conventional nitroarenes by lithiated enolates derived from methyl vinyl ketones easily takes place, following a formal (4+2) cycloaddition process. While nitroindoles react readily with in situ generated conjugated enolates, the deaggregation of these latter species using HMPA extends the reaction scope to the more aromatic nitronaphthalenes and pyridines.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02156509
Contributor : Madeleine Roux-Merlin <>
Submitted on : Friday, June 14, 2019 - 2:07:08 PM
Last modification on : Thursday, July 2, 2020 - 3:19:22 AM

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Karine Pasturaud, Batoul Rkein, Morgane Sanselme, Muriel Sebban, Sami Lakhdar, et al.. The facile dearomatization of nitroaromatic compounds using lithium enolates of unsaturated ketones in conjugate additions and (4+2) formal cycloadditions. Chemical Communications, Royal Society of Chemistry, 2019, 55 (52), pp.7446-7449. ⟨10.1039/C9CC02924A⟩. ⟨hal-02156509⟩

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