Synthesis, structure and magnetic behavior of iron arsenites with hierarchical magnetic units

Leclercq, Bastien; Kabbour, Houria; Arévalo‐López, Ángel M.; Daviero‐Minaud, Sylvie; Minaud, Claire; Rooney, David; Mentré, Olivier

doi:10.1039/d0qi00887g

Cited by 8 publications

(4 citation statements)

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“…In terms of C(sp 3 )-H precursors, we rst explored various electronically and sterically diverse ethylbenzene derivatives (Table 2). These reactions, under standard conditions, produced coupling products (44)(45)(46)(47)(48)(49)(50)(51)(52)(53)(54)(55)(56)(57) with yields of 55-74%. Additionally, alkyl benzenes with a long side chain (58, 59), fused aliphatic rings (60-62), fused aromatic rings (63), as well as tertiary or primary benzylic C-H bonds (64-66), were found to be compatiable, delivering products with yields of 49-65%.…”

Section: Resultsmentioning

confidence: 99%

“…It is worth mentioning that these products did not form in the dark. In the presence of 1d, a C(sp 2 )-H precursor, (1-chloroethyl)benzene or its bromide analog could be easily converted to the cross-coupling product (44) in a good yield (Fig. 3f).…”

Section: Resultsmentioning

confidence: 99%

“…Aerobic oxidation of the iron(II) species regenerates the iron(III) salt, which can further oxidize the C-centered radical to a carbon cation. [44][45][46] Subsequently, the C(sp 2 )-C(sp 3 ) cross-coupling coupling of the alkyl carbon cation, or a corresponding chloride derivative from nucleophile attack, with arenes leads to product formation. The nal step can be viewed as a Friedel-Crafts-type process promoted by an iron-based Lewis acid.…”

Section: Resultsmentioning

confidence: 99%

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Visible light-triggered selective C(sp2)-H/C(sp3)-H coupling of benzenes with aliphatic hydrocarbons

Gong

Cheng

et al. 2023

Preprint

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The direct and selective coupling of benzenes with aliphatic hydrocarbons is a promising strategy for C(sp2)-C(sp3) bond formation using readily available starting materials, yet it remains a significant challenge. In this study, we have developed a simplified photochemical system that incorporates catalytic amounts of iron(III) halides as multifunctional reagents and air as a green oxidant to address this synthetic problem. The reaction between a variety of low reactive C(sp2)-H precursors with C(sp3)-H donors has been achieved under mild conditions. The iron halide acts as a multifunctional reagent that responds to visible light, initiates C-centered radicals, induces single-electron oxidation to carbocations, and participates in a subsequent Friedel-Crafts-type process. The gradual release of radical species and carbocation intermediates appears to be critical for achieving desirable reactivity and selectivity. This eco-friendly, cost-efficient approach offers access to various building blocks from abundant hydrocarbon feedstocks, and demonstrates the potential of iron halides in sustainable synthesis.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Visible light-triggered selective C(sp2)-H/C(sp3)-H coupling of benzenes with aliphatic hydrocarbons

Gong

Cheng

et al. 2023

Preprint

View full text Add to dashboard Cite

show abstract

“…This active radical abstracts a hydrogen atom from an aliphatic C-H bond, affording HCl and a C-centered radical. Aerobic oxidation of the iron(II) species regenerates the iron(III) salt, which can further oxidize the C-centered radical to a carbon cation [47][48][49] . Subsequently, the C(sp 2 )-C(sp 3 ) cross-coupling coupling of the alkyl carbon cation, or a corresponding chloride derivative from nucleophile attack, with arenes leads to product formation.…”

Section: Mechanistic Studiesmentioning

confidence: 99%

Visible light-triggered selective C(sp2)-H/C(sp3)-H coupling of benzenes with aliphatic hydrocarbons

Li,

Cheng,

et al. 2023

Nat Commun

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The direct and selective coupling of benzenes with aliphatic hydrocarbons is a promising strategy for C(sp2)-C(sp3) bond formation using readily available starting materials, yet it remains a significant challenge. In this study, we have developed a simplified photochemical system that incorporates catalytic amounts of iron(III) halides as multifunctional reagents and air as a green oxidant to address this synthetic problem. Under mild conditions, the reaction between a strong C(sp2)-H bond and a robust C(sp3)-H bond has been achieved, affording a broad range of cross-coupling products with high yields and commendable chemo-, site-selectivity. The iron halide acts as a multifunctional reagent that responds to visible light, initiates C-centered radicals, induces single-electron oxidation to carbocations, and participates in a subsequent Friedel-Crafts-type process. The gradual release of radical species and carbocation intermediates appears to be critical for achieving desirable reactivity and selectivity. This eco-friendly, cost-efficient approach offers access to various building blocks from abundant hydrocarbon feedstocks, and demonstrates the potential of iron halides in sustainable synthesis.

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Valence-dependent dynamics: quantitatively understanding arsenic reallocations on iron oxyhydroxide mediated by microbial respiration

Hong,

Liu,

et al. 2024

Chemical Geology

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Synthesis, structure and magnetic behavior of iron arsenites with hierarchical magnetic units

Abstract: The standard redox potentials of the Fe3+/Fe2+ (+0.77 V) and H3AsO4/H3AsO3 (+0.56 V) stabilize the easy crystallization of ferric arsenates. However, activating solvothermal reactions with a reducing agent such as...

Cited by 8 publications

References 54 publications

Visible light-triggered selective C(sp2)-H/C(sp3)-H coupling of benzenes with aliphatic hydrocarbons

Visible light-triggered selective C(sp2)-H/C(sp3)-H coupling of benzenes with aliphatic hydrocarbons

Visible light-triggered selective C(sp2)-H/C(sp3)-H coupling of benzenes with aliphatic hydrocarbons

Valence-dependent dynamics: quantitatively understanding arsenic reallocations on iron oxyhydroxide mediated by microbial respiration

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