Well-Defined Aryl-FeII Complexes in Cross-Coupling and C–H Activation Processes

Herein we explore the intrinsic organometallic reactivity of iron embedded in a tetradentate N3C macrocyclic ligand scaffold that allows the stabilization of aryl-Fe species, which are key intermediates in Fe-catalyzed cross-coupling and C–H functionalization processes. This study covers C–H activat...

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Bibliographic Details
Published in:Organometallics 2021-05, Vol.40 (9), p.1195-1200
Main Authors: Magallón, Carla, Planas, Oriol, Roldán-Gómez, Steven, Luis, Josep M., Company, Anna, Ribas, Xavi
Format: Article
Language:English
Subjects:
Communication
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Summary:Herein we explore the intrinsic organometallic reactivity of iron embedded in a tetradentate N3C macrocyclic ligand scaffold that allows the stabilization of aryl-Fe species, which are key intermediates in Fe-catalyzed cross-coupling and C–H functionalization processes. This study covers C–H activation reactions using Me L H and FeCl2, biaryl C–C coupling product formation through reaction with Grignard reagents, and cross-coupling reactions using Me L Br or H L Br in combination with Fe0(CO)5. Synthesis under light irradiation and moderate heating (50 °C) affords the aryl-FeII complexes [FeII(Br)­( Me L)­(CO)] (1 Me ) and [FeII( H L)­(CO)2]Br (1 H ). Exhaustive spectroscopic characterization of these rare low-spin diamagnetic species, including their crystal structures, allowed the investigation of their intrinsic reactivity.
ISSN:0276-7333
1520-6041
DOI:10.1021/acs.organomet.1c00100