Structure and C–C cross-coupling reactivity of iron(III) complexes of halogenated amine-bis(phenolate) ligands

Reckling, Amy M.; Martin, D. W.; Dawe, Louise N.; Decken, Andreas; Kozak, Christopher M.

doi:10.1016/j.jorganchem.2010.09.076

Cited by 47 publications

(37 citation statements)

References 73 publications

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“…Iron(III) halide compounds supported by tetradentate (amine)bis(phenolato) ligands showed good activity as catalysts for the cross-coupling of aryl Grignards with primary and secondary alkyl halides, [68] but the presence of halide groups on the phenolato groups leads to decreased activity. [70] With these systems, diethyl ether was superior to THF as a solvent for the cross-coupling reactions. Also, it was found that reactions performed at room temperature or higher gave superior results to those conducted at lower temperatures.…”

Section: Cross-coupling Catalysis Studiesmentioning

confidence: 99%

“…Recently, we reported on Fe III compounds supported by tetradentate and tridentate (amine)bis(phenolato) ligands, which are effective catalysts for cross-coupling of aryl Grignard reagents with alkyl halides, including secondary alkyl halides and benzyl halides. [68][69][70] We therefore began investigating whether (amine)bis(phenolato)iron(acac) complexes would be active single-component catalysts for C-C cross coupling of aryl Grignard reagents with alkyl halides. Herein we report the synthesis and structural, spectroscopic, and electrochemical characterization of a series of these complexes and preliminary studies of their C-C cross coupling activity.…”

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confidence: 99%

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Synthesis, Structure, and C–C Cross‐Coupling Activity of (Amine)bis(phenolato)iron(acac) Complexes

2011

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A series of (amine)bis(phenolato)iron(III)acac complexes has been prepared and characterized. Reaction of Fe(acac)3 with the diprotonated linear tetradentate proligand N,N′‐bis(4,6‐di‐tert‐butyl‐2‐methylphenol)‐N,N′‐dimethyl‐1,2‐diaminoethane, H2[L1], and tripodal tetradentate ligand precursors dimethylaminoethylamino‐N,N‐bis(2‐methylene‐4,6‐di‐tert‐butylphenol), H2[L2], dimethylaminoethylamino‐N,N‐bis(2‐methylene‐4‐methyl‐6‐tert‐butylphenol), H2[L3], 2‐methoxyethylamino‐N,N‐bis(2‐methylene‐4,6‐di‐tert‐butylphenol), H2[L4], 2‐methoxyethylamino‐N,N‐bis(2‐methylene‐4‐methyl‐6‐tert‐butylphenol), H2[L5], and 2‐methoxyethylamino‐N,N‐bis(2‐methylene‐4,6‐dimethylphenol), H2[L6], produces the distorted octahedral FeIII complexes [L1]Fe(acac) (1), [L2]Fe(acac) (2), [L3]Fe(acac) (3), [L4]Fe(acac) (4), [L5]Fe(acac) (5), and [L6]Fe(acac) (6). In all of these complexes, the phenolato oxygen atoms are cis‐oriented. The paramagnetic FeIII complexes 1–6 were also characterized by UV/Vis and IR spectroscopy, mass spectrometry, cyclic voltammetry, and magnetic measurements. Single crystal X‐ray molecular structures have been determined for complexes 1, 2, 3, 5, and the proligand H2[L6]. Preliminary investigations of complexes 1–6 for catalytic cross‐coupling reactions of aryl Grignard reagents with cyclic and acyclic secondary alkyl halides and benzyl halides were performed. While the activity for cyclohexyl chlorides and bromides was high, cross‐coupling of benzyl halides was moderate and 2‐bromo‐ and 2‐chlorobutane gave poor yields of cross‐coupled product.

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Section: Cross-coupling Catalysis Studiesmentioning

confidence: 99%

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Synthesis, Structure, and C–C Cross‐Coupling Activity of (Amine)bis(phenolato)iron(acac) Complexes

2011

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“…39 Elemental analyses for C, H, and N were obtained on a Perkin-Elmer analyzer model 240. 39 Elemental analyses for C, H, and N were obtained on a Perkin-Elmer analyzer model 240.…”

Section: Methodsmentioning

confidence: 99%

A molecular cobalt catalyst supported by an amine-bis(phenolate) ligand for both electrolytic and photolytic water reduction

Zhou

Zhan

2015

RSC Adv.

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A new molecular catalyst based on cobalt complex [L 2 Co 2 Cl 2 ] 1 is prepared by the reaction of an aminebis(phenolate) ligand (H 2 L) with CoCl 2 $6H 2 O for both electrolytic and photolytic water reduction. 1 can electrocatalyze hydrogen evolution from water with a turnover frequency (TOF) of 789.6 moles of hydrogen per mole of catalyst per hour at an overpotential of 837.6 mV (pH 7.0). 1 in a pH 6.0 aqueous solution under air, together with [Ru(bpy) 3 ]Cl 2 and ascorbic acid, in the presence of blue light (l max ¼ 469 nm) also produces hydrogen with a turnover number (TON) ¼ 912 mol of H 2 (mol of cat) À1 .Scheme 1 Schematic representation of the synthesis of [L 2 Co 2 Cl 2 ] 1.

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“…Kozak and co-workers described the synthesis of Fe III complexes of these ligands, and their use as efficient C-C bond-forming catalysts in the coupling of alkyl halides with aryl Grignard reagents (41,42).…”

Section: Amine-bis(phenolate)-supported Iron Complexesmentioning

confidence: 99%

The Interplay of ATRP, OMRP and CCT in Iron-Mediated Controlled Radical Polymerization

Lake

Shaver

2015

ACS Symposium Series

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Structure and C–C cross-coupling reactivity of iron(III) complexes of halogenated amine-bis(phenolate) ligands

Cited by 47 publications

References 73 publications

Synthesis, Structure, and C–C Cross‐Coupling Activity of (Amine)bis(phenolato)iron(acac) Complexes

Synthesis, Structure, and C–C Cross‐Coupling Activity of (Amine)bis(phenolato)iron(acac) Complexes

A molecular cobalt catalyst supported by an amine-bis(phenolate) ligand for both electrolytic and photolytic water reduction

The Interplay of ATRP, OMRP and CCT in Iron-Mediated Controlled Radical Polymerization

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