The reaction of CpFe(CO)2X(X  Cl, Br, I) with phosphines catalyzed by [CpFe(CO)2]2: evidence for an electron transfer chain catalysis mechanism

Gipson, Stephen L.; Liu, Ling‐Kang; Soliz, Raul U

doi:10.1016/s0022-328x(96)06586-2

Cited by 21 publications

(17 citation statements)

References 35 publications

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“…The only isolated and identified product containing phosphine was [{h 4 -(C 6 F 5 )C 5 H 5 }Fe(CO) 2 PEt 3 ] (yield 5 %). Complexes of this type have recently been obtained with high yield in the three-component reaction of FpHal, RLi and R 3 P, [27] and adopting the mechanism proposed [28] the formation of the complex in our case is described in Scheme 4. The detection of such a complex provides extra evidence for HME in the reaction.…”

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confidence: 95%

The Reaction of the [CpFe(CO)2]− Anion with Pentafluorochlorobenzene: Nucleophilic Aromatic Substitution by Halogen-Metal Exchange

et al. 1998

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confidence: 95%

The Reaction of the [CpFe(CO)2]− Anion with Pentafluorochlorobenzene: Nucleophilic Aromatic Substitution by Halogen-Metal Exchange

et al. 1998

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“…[15] Similarly, catalytic substitution of the halide ligands of CpFe(CO) 2 X( X= CI, 8a;X= Br, 8b;X= I, 8c)w ith triphenylphosphinet oa fford complex 9 proceeds through am echanism that involves an electron-transfer chain (Scheme 3b). [16] The properties of these complexes to generater adical species can be exploited to induce apoptosis in breast cancer cells and HeLa cell lines, whilst normalc ellsr emained unaffected. [17] Interestingly,c omplex CpFe(CO) 2 I( 8c)w as metabolically stable and easily permeateda cross alipid barrier.…”

Section: Radical Reactions Promoted By Iron(ii) Complexesmentioning

confidence: 99%

“…Unsaturated trichloroacetates (16,18)t hat contained different carbon chains were cyclized through an ATRA (atom-transfer radical addition) reactioni nt he presence of FeCl 2 (3-10 mol %) in 1,2-dichloroethane (DCE) at 80 8C. Five-, eight-, nine-, and ten-membered lactones (17,19)w ere obtainedi n moderate yields (up to 55 %f or the five-membered ring; Scheme6).…”

Section: Radical Cyclization Reactions Mediated By Iron(ii) Saltsmentioning

confidence: 99%

Iron‐Promoted Radical Reactions: Current Status and Perspectives

2017

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Catalysis based on precious metals has reached an incredible level of sophistication and has found widespread use and application,b oth in academia andi ni ndustry.H owever,o wing to the environmental impact, cost, and low abundance, catalysis based on inexpensive, abundant,a nd environmentally benign first-row transition metals has become av aluable alternative to traditional reactions promoted by their less-abundantc ounterparts. From economic and ecological perspectives, iron salts and iron metal complexes are highly promising candidates to replace costly and toxic metals. In recent years, iron complexes have been used to promote the formation of radicals. Photoredox chemistry is av aluablem ethod for the generation of radical species under mild conditions, but it often relies on rare-earth-metal complexes.T he employment of iron complexes for the generation of radicals is attractive for the development of sustainable, simple, and effective procedures.I nt his Focus Review,w eh ighlight and summarize recent radicalr eactions promoted by iron complexes and their application in organic reactions.

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“…The formation of salt products in the reaction can be explained by a modification of step (ii) above in which addition of PR 3 takes place prior to CO loss. Thus the modified reaction entails formation of a 19 electron intermediate either via an electron transfer chain catalysed reaction [16] or as shown in Scheme 3.…”

Section: Reaction Mechanismmentioning

confidence: 99%

Solvent-free Substitution Reactions of Solid Phosphines with (η⁵-RC₅H₄)Fe(CO)₂I (R = H, Me) Complexes

Munyaneza

Bala

Coville

2007

Zeitschrift Für Naturforschung B

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Dedicated to Prof. Helgard G. Raubenheimer on the occasion of his 65 th birthdayfriend and colleague over many decadesReactions of (η 5 -RC 5 H 4 )Fe(CO) 2 I (R = H, Me) complexes with phosphine ligands PR 3 (R = Ph, m-Tol, p-C 6 H 4 OMe, p-C 6 H 4 Cl, p-C 6 H 4 F) have been performed under solvent-free conditions in the melt phase and generally yielded the ionic products [(η 5 -RC 5 H 4 )Fe(CO) 2 PR 3 ]I rather than the CO substituted products (η 5 -RC 5 H 4 )Fe(CO)(PR 3 )I. The complexes have been characterised by IR, NMR and MS techniques. By contrast, the same reactions studied in benzene solution have yielded mainly the CO substitution products. Factors that affect the solvent-free reaction include variation in R and R , reaction temperature and the addition of [CpFe(CO) 2 ] 2 as a catalyst. The mechanism of the reaction for the formation of the ionic complex is proposed to go via a 19 electron intermediate. This is in contrast to the reaction in bezene that occurs via a 17 electron intermediate, clearly indicating the role of the melt phase in the reaction.

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The reaction of CpFe(CO)2X(X  Cl, Br, I) with phosphines catalyzed by [CpFe(CO)2]2: evidence for an electron transfer chain catalysis mechanism

Cited by 21 publications

References 35 publications

The Reaction of the [CpFe(CO)2]− Anion with Pentafluorochlorobenzene: Nucleophilic Aromatic Substitution by Halogen-Metal Exchange

The Reaction of the [CpFe(CO)2]− Anion with Pentafluorochlorobenzene: Nucleophilic Aromatic Substitution by Halogen-Metal Exchange

Iron‐Promoted Radical Reactions: Current Status and Perspectives

Solvent-free Substitution Reactions of Solid Phosphines with (η⁵-RC₅H₄)Fe(CO)₂I (R = H, Me) Complexes

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The reaction of CpFe(CO)2X(X  Cl, Br, I) with phosphines catalyzed by [CpFe(CO)2]2: evidence for an electron transfer chain catalysis mechanism

Cited by 21 publications

References 35 publications

The Reaction of the [CpFe(CO)2]− Anion with Pentafluorochlorobenzene: Nucleophilic Aromatic Substitution by Halogen-Metal Exchange

The Reaction of the [CpFe(CO)2]− Anion with Pentafluorochlorobenzene: Nucleophilic Aromatic Substitution by Halogen-Metal Exchange

Iron‐Promoted Radical Reactions: Current Status and Perspectives

Solvent-free Substitution Reactions of Solid Phosphines with (η5-RC5H4)Fe(CO)2I (R = H, Me) Complexes

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Solvent-free Substitution Reactions of Solid Phosphines with (η⁵-RC₅H₄)Fe(CO)₂I (R = H, Me) Complexes