Elucidating Dramatic Ligand Effects on SET Processes: Iron Hydride versus Iron Borohydride Catalyzed Reductive Radical Cyclization of Unsaturated Organic Halides

Abstract : An iron(II) borohydride complex ([(η1-H3BH)FeCl(NCCH3)4]) is employed as the precatalyst in iron-catalyzed radical cyclizations of unsaturated organic halides in the presence of NaBH4. Mechanistic investigations have established that the ligand bound to the metal center (acetonitrile versus ethylenebis(diphenylphosphine) (dppe)) plays a crucial role in the structure and reactivity of the active anionic iron(I) hydride ([HFeCl(dppe)2]−) and borohydride ([(η1-H3BH)FeCl(NCCH3)4]−) with unsaturated haloacetals. This work provides new insights into iron(I) hydride and borohydride species and their potential implication in single-electron processes.
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Submitted on : Tuesday, October 3, 2017 - 7:08:46 AM
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Sara Kyne, Martin Clémancey, Geneviève Blondin, Etienne Derat, Louis Fensterbank, et al.. Elucidating Dramatic Ligand Effects on SET Processes: Iron Hydride versus Iron Borohydride Catalyzed Reductive Radical Cyclization of Unsaturated Organic Halides. Organometallics, American Chemical Society, 2017, 37, pp.761-771. ⟨http://dx.doi.org/10.1021/acs.organomet.7b00603⟩. ⟨10.1021/acs.organomet.7b00603⟩. ⟨cea-01608951⟩

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