Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Selectivity of C-H versus C-F Bond Oxygenation by Homo- and Heterometallic Fe4 , Fe3 Mn, and Mn4 Clusters.

Literature DB >> 28658508

Selectivity of C-H versus C-F Bond Oxygenation by Homo- and Heterometallic Fe₄ , Fe₃ Mn, and Mn₄ Clusters.

Graham de Ruiter¹, Kurtis M Carsch¹, Michael K Takase¹, Theodor Agapie¹.

Abstract

A series of tetranuclear [LM3 (HFArPz)3 OM'][OTf]2 (M, M'=Fe or Mn) clusters that displays 3-(2-fluorophenyl)pyrazolate (HFArPz) as bridging ligand is reported. With these complexes, manganese was demonstrated to facilitate C(sp2 )-F bond oxygenation via a putative terminal metal-oxo species. Moreover, the presence of both ortho C(sp2 )-H and C(sp2 )-F bonds in proximity of the apical metal center provided an opportunity to investigate the selectivity of intramolecular C(sp2 )-X bond oxygenation (X=H or F) in these isostructural compounds. With iron as the apical metal center, (M'=Fe) C(sp2 )-F bond oxygenation occur almost exclusively, whereas with manganese (M'=Mn), the opposite reactivity is preferred.

Entities: CellLine Chemical Disease Gene Mutation Species

Keywords: cluster compounds; dehalogenation; multimetallic complexes; oxygen atom transfer; oxygenation

Year: 2017 PMID： 28658508 PMCID： PMC5659184 DOI： 10.1002/chem.201702302

Source DB: PubMed Journal: Chemistry ISSN： 0947-6539 Impact factor: 5.236

56 in total

1. Combined experimental and theoretical study on aromatic hydroxylation by mononuclear nonheme iron(IV)-oxo complexes.

Authors: Sam P de Visser; Kyungeun Oh; Ah-Rim Han; Wonwoo Nam
Journal: Inorg Chem Date: 2007-04-20 Impact factor: 5.165

2. Occurrence of the NIH shift upon the cytochrome P450-catalyzed in vivo and in vitro aromatic ring hydroxylation of fluorobenzenes.

Authors: J Koerts; A E Soffers; J Vervoort; A De Jager; I M Rietjens
Journal: Chem Res Toxicol Date: 1998-05 Impact factor: 3.739

Review 3. P450 enzymes: their structure, reactivity, and selectivity-modeled by QM/MM calculations.

Authors: Sason Shaik; Shimrit Cohen; Yong Wang; Hui Chen; Devesh Kumar; Walter Thiel
Journal: Chem Rev Date: 2010-02-10 Impact factor: 60.622

4. Hydroxylation of aromatics with the help of a non-haem FeOOH: a mechanistic study under single-turnover and catalytic conditions.

Authors: Aurore Thibon; Véronique Jollet; Caroline Ribal; Katell Sénéchal-David; Laurianne Billon; Alexander B Sorokin; Frédéric Banse
Journal: Chemistry Date: 2012-01-30 Impact factor: 5.236

5. Cytochrome P450-mediated oxidation of pentafluorophenol to tetrafluorobenzoquinone as the primary reaction product.

Authors: C den Besten; P J van Bladeren; E Duizer; J Vervoort; I M Rietjens
Journal: Chem Res Toxicol Date: 1993 Sep-Oct Impact factor: 3.739

Review 6. Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001-2011).

Authors: Jiang Wang; María Sánchez-Roselló; José Luis Aceña; Carlos del Pozo; Alexander E Sorochinsky; Santos Fustero; Vadim A Soloshonok; Hong Liu
Journal: Chem Rev Date: 2013-12-03 Impact factor: 60.622

Selectivity of C-H versus C-F Bond Oxygenation by Homo- and Heterometallic Fe₄ , Fe₃ Mn, and Mn₄ Clusters.

1. Combined experimental and theoretical study on aromatic hydroxylation by mononuclear nonheme iron(IV)-oxo complexes.

2. Occurrence of the NIH shift upon the cytochrome P450-catalyzed in vivo and in vitro aromatic ring hydroxylation of fluorobenzenes.

Review 3. P450 enzymes: their structure, reactivity, and selectivity-modeled by QM/MM calculations.

4. Hydroxylation of aromatics with the help of a non-haem FeOOH: a mechanistic study under single-turnover and catalytic conditions.

5. Cytochrome P450-mediated oxidation of pentafluorophenol to tetrafluorobenzoquinone as the primary reaction product.

Review 6. Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001-2011).

Review 7. Hydrocarbon hydroxylation by cytochrome P450 enzymes.

8. Oxygen activation by nonheme iron(II) complexes: alpha-keto carboxylate versus carboxylate.

Review 9. Mn4Ca cluster in photosynthesis: where and how water is oxidized to dioxygen.

10. Direct observation of a nonheme iron(IV)-oxo complex that mediates aromatic C-F hydroxylation.

Review 1. Carbon-fluorine bond cleavage mediated by metalloenzymes.