Berthold Hoge

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First Main‐Group Element Lewis Acid Thionyl Chloride Adduct and its Chemistry

Katharina Tölke, Sven Porath, Beate Neumann, Hans‐Georg Stammler, more

Angewandte Chemie International Edition > 63 > 41 > n/a - n/a

Although the adduct of aluminum trichloride with thionyl chloride has been reported, no thionyl chloride adduct of a main group element Lewis acid or organometallic compound has been structurally characterized. In this communication we present the synthesis and reactivity of the structurally ascertained adduct of thionyl chloride with tris(pentafluoroethyl)gallane as a representative of a main group...

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First Main‐Group Element Lewis Acid Thionyl Chloride Adduct and its Chemistry

Katharina Tölke, Sven Porath, Beate Neumann, Hans‐Georg Stammler, more

Angewandte Chemie > 136 > 41 > n/a - n/a

Although the adduct of aluminum trichloride with thionyl chloride has been reported, no thionyl chloride adduct of a main group element Lewis acid or organometallic compound has been structurally characterized. In this communication we present the synthesis and reactivity of the structurally ascertained adduct of thionyl chloride with tris(pentafluoroethyl)gallane as a representative of a main group...

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Water‐Stable Lewis Superacids as Precursors for (Pseudo)halogenogallate and ‐indate Salts

Katharina Tölke, Sven Porath, Beate Neumann, Hans‐Georg Stammler, more

European Journal of Inorganic Chemistry > 27 > 21 > n/a - n/a

Tris(pentafluoroethyl)indane dihydrate, [In(C₂F₅)₃(OH₂)₂], and the gallium analog, [Ga(C₂F₅)₃(OH₂)₂], serve as transfer reagents for the In(C₂F₅)₃ and Ga(C₂F₅)₃ units, as illustrated by the preparation of salts of (pseudo)halogenotris(pentafluoroethyl)indate and ‐gallate anions, [M(C₂F₅)₃)X]⁻ (M=Ga, In; X=F, Cl, Br, I, CN, SCN). Due to the water tolerance and water solubility of [In(C₂F₅)₃(OH₂)₂]...

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Water Adducts of the Lewis Superacids: Tris(pentafluoroethyl)gallane and ‐indane

Katharina Tölke, Sven Porath, Yury V. Vishnevskiy, Beate Neumann, more

European Journal of Inorganic Chemistry > 27 > 12 > n/a - n/a

Lewis superacids (LSA) are defined by a fluoride ion affinity (FIA) that exceeds that of SbF₅, and are thus characterized as hard according to the HSAB concept. Soft superacidity was defined for compounds exceeding the hydride ion affinity (HIA) of B(C₆F₅)₃. Herein we report on the synthesis of a Lewis acid being superacidic only on the soft regime: tris(pentafluoroethyl)indane, In(C₂F₅)₃. It is accessible...

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Gallate and Indate Salts with Unsaturated Electron Withdrawing Groups

Sven Porath, Beate Neumann, Hans‐Georg Stammler, Berthold Hoge

European Journal of Inorganic Chemistry > 27 > 5 > n/a - n/a

The introduction of a number of unsaturated fluorinated and chlorinated substituents onto gallium and indium was investigated. Gallate, [GaR₄]⁻, and indate, [InR₄]⁻, anions with trifluorovinyl (CF=CF₂), 1‐chloro‐2,2‐difluorovinyl (CCl=CF₂), (E)‐pentafluoropropen‐1‐yl (E‐CF=CFCF₃), 3,3,3‐trifluoropropynyl (C≡C−CF₃) and dichloromethyl (CHCl₂) substituents were synthesized and isolated as the respective...

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Synthesis and Characterization of Tetrakis(pentafluoroethyl)indate Salts

Sven Porath, Mira Keßler, Beate Neumann, Hans‐Georg Stammler, more

Chemistry – A European Journal > 29 > 20 > n/a - n/a

In the rising field of organoindium chemistry little is known about the perfluoroorganyl‐substituted indium compounds. The increasing use of indium reagents is explained by their high stability and tolerance towards water and functional groups. Here we report on the synthesis of the novel tetrakis(pentafluoroethyl)indate, [In(C₂F₅)₄]⁻, and its characterization in salts with the cations [Li(thf)₃]⁺...

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Frontispiece: Oxidative Additions of C−F Bonds to the Silanide Anion [Si(C₂F₅)₃]⁻

Natalia Tiessen, Mira Keßler, Beate Neumann, Hans‐Georg Stammler, more

Angewandte Chemie International Edition > 61 > 17 > n/a - n/a

Silicon In their Research Article (e202116468), Berthold Hoge et al. report oxidative additions of [Si(C₂F₅)₃]⁻ to aryl‐ and alkenylfluorides, enabling the isolation of tetraorganofluorosilicate salts devoid of chelating ligands.

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Oxidative Additions of C−F Bonds to the Silanide Anion [Si(C₂F₅)₃]⁻

Natalia Tiessen, Mira Keßler, Beate Neumann, Hans‐Georg Stammler, more

Angewandte Chemie International Edition > 61 > 17 > n/a - n/a

Compounds exhibiting main group elements in low oxidation states were found to mimic the reactivity of transition metal complexes. Like the latter, such main group species show a proclivity of changing their oxidation state as well as their coordination number by +2, therefore fulfilling the requirements for oxidative additions. Prominent examples of such main group compounds that undergo oxidative...

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Frontispiz: Oxidative Addition von C−F‐Bindungen an das Silanid‐Anion [Si(C₂F₅)₃]⁻

Natalia Tiessen, Mira Keßler, Beate Neumann, Hans‐Georg Stammler, more

Angewandte Chemie > 134 > 17 > n/a - n/a

Silicium In ihrem Forschungsartikel (e202116468) berichten Berthold Hoge et al. über oxidative Additionen von [Si(C₂F₅)₃]⁻ an Aryl‐ und Alkenylfluoride, welche die Isolierung von Tetraorganofluorosilicatsalzen frei von chelatisierende Liganden ermöglichen.

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Oxidative Addition von C−F‐Bindungen an das Silanid‐Anion [Si(C₂F₅)₃]⁻

Natalia Tiessen, Mira Keßler, Beate Neumann, Hans‐Georg Stammler, more

Angewandte Chemie > 134 > 17 > n/a - n/a

Verbindungen von Hauptgruppenelementen in niedrigen Oxidationsstufen sind in der Lage, die Reaktivität von Übergangsmetallkomplexen nachzuahmen. Wie Letztere neigen niedervalente Hauptgruppenelementverbindungen zur Änderung ihrer Oxidationsstufe und Koordinationszahl um +2, wodurch sie die wesentlichen Voraussetzungen für oxidative Additionen erfüllen. Prominente Beispiele für Hauptgruppenelementverbindungen,...

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Synthesis, Reactivity and Structural Properties of Trifluoromethylphosphoranides

Oleg O. Shyshkov, Alexander A. Kolomeitsev, Berthold Hoge, Enno Lork, more

Chemistry – A European Journal > 28 > 14 > n/a - n/a

Phosphoranides are interesting hypervalent species which serve as model compounds for intermediates or transition states in nucleophilic substitution reactions at trivalent phosphorus substrates. Herein, the syntheses and properties of stable trifluoromethylphosphoranide salts are reported. [K(18‐crown‐6)][P(CF₃)₄], [K(18‐crown‐6)][P(CF₃)₃F], and [NMe₄][P(CF₃)₂F₂] were obtained by treatment of trivalent...

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Cover Feature: Tetrakis(pentafluoroethyl)gallate, [Ga(C₂F₅)₄]⁻, Ionic Liquids (Chem. Eur. J. 53/2021)

Harry Biller, Swantje Lerch, Katharina Tölke, Hans‐Georg Stammler, more

Chemistry – A European Journal > 27 > 53 > 13277 - 13277

New imidazolium‐based tunable aryl alkyl ionic liquids (TAAILs) containing the weakly coordinating anion [Ga(C₂F₅)₄]⁻ are reported. Some phenyl derivatives in combination with different alkyl chains were investigated with regard to their viscosity, conductivity and electrochemical window. In contrast to gallates with standard cations (EMIM, BMIM) the gallate‐TAAILs are stable even up to high electrochemical...

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Tetrakis(pentafluoroethyl)gallate, [Ga(C₂F₅)₄]⁻, Ionic Liquids

Harry Biller, Swantje Lerch, Katharina Tölke, Hans‐Georg Stammler, more

Chemistry – A European Journal > 27 > 53 > 13325 - 13329

We synthesized new imidazolium‐based tunable aryl alkyl ionic liquids (TAAILs) with the weakly coordinating tetrakis(pentafluoroethyl)gallate anion, [Ga(C₂F₅)₄]⁻. Phenyl and phenyl derivatives (2‐Me, 4‐OMe, 2,4‐F) were combined with varying alkyl chain lengths at the imidazolium core leading to TAAILs, which were investigated with regard to their viscosity, conductivity, and electrochemical window...

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Cover Feature: Tris(pentafluoroethyl)silanol Derivatives and the Lewis Amphoteric Tris(pentafluoroethyl)silanolate Anion, [Si(C₂F₅)₃O]⁻ (Chem. Eur. J. 43/2021)

Natalia Tiessen, Nico Schwarze, Mira Keßler, Beate Neumann, more

Chemistry – A European Journal > 27 > 43 > 11018 - 11018

The tris(pentafluoroethyl)silanol, Si(C₂F₅)₃OH, flashes out of the shadows of silanol derivatives in the cover image, paving the way to its disiloxane and disilanolate. Oxidation of tris(pentafluoroethyl)silane, Si(C₂F₅)₃H, with NO₂ provides Si(C₂F₅)₃OH, which readily condenses to disiloxane (C₂F₅)₃SiOSi(C₂F₅)₃. Deprotonation of in situ generated Si(C₂F₅)₃OH yields disilanolate [{Si(C₂F₅)₃O}₂]²⁻ underlining...

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Tris(pentafluoroethyl)silanol Derivatives and the Lewis Amphoteric Tris(pentafluoroethyl)silanolate Anion, [Si(C₂F₅)₃O]⁻

Natalia Tiessen, Nico Schwarze, Mira Keßler, Beate Neumann, more

Chemistry – A European Journal > 27 > 43 > 11041 - 11044

While alkyl‐substituted siloxanes are widely known, virtually nothing is known about perfluoroalkyl siloxanes and their congener species, the silanols and silanolates. We recently reported on the tris(pentafluoroethyl)silanide ion, [Si(C₂F₅)₃]⁻, which features Lewis amphoteric character deriving from the pentafluoroethyl substituents and their strong electron‐withdrawing properties. Transferring this...

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Phosphorus‐Containing Superbases: Recent Progress in the Chemistry of Electron‐Abundant Phosphines and Phosphazenes

Robin F. Weitkamp, Beate Neumann, Hans‐Georg Stammler, Berthold Hoge

Chemistry – A European Journal > 27 > 42 > 10807 - 10825

The renaissance of Brønsted superbases is primarily based on their pronounced capacity for a large variety of chemical transformations under mild reaction conditions. Four major set screws are available for the selective tuning of the basicity: the nature of the basic center (N, P, …), the degree of electron donation by substituents to the central atom, the possibility of charge delocalization, and...

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Frontispiece: Phosphorus‐Containing Superbases: Recent Progress in the Chemistry of Electron‐Abundant Phosphines and Phosphazenes

Robin F. Weitkamp, Beate Neumann, Hans‐Georg Stammler, Berthold Hoge

Chemistry – A European Journal > 27 > 42 > n/a - n/a

Forged in fire. Flaming phosphorus is the hottest element of current Lewis and Brønsted superbase design. The electron abundancy makes these compounds highly important tools as ligands or as auxiliary bases in chemical catalysis and thus enables a great variety of so far unimagined chemical transformations. This synthetically informed minireview gives insight into the recent development of phosphorus‐containing...

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Evidence of the Lewis‐Amphoteric Character of Tris(pentafluoroethyl)silanide, [Si(C₂F₅)₃]⁻

Natalia Tiessen, Mira Keßler, Beate Neumann, Hans‐Georg Stammler, more

Angewandte Chemie International Edition > 60 > 21 > 12124 - 12131

According to a first view on the geometrical and electronic structure of the tris(pentafluoroethyl)silanide, this anion appears as a Lewis base. Quantum chemical calculations on perfluoroalkylated silanides show significantly lower HOMO and LUMO energy levels in comparison to their non‐fluorinated counterparts, which implies reduced Lewis basicity and increased Lewis acidity of the [Si(C₂F₅)₃]⁻ ion...

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Cover Picture: Evidence of the Lewis‐Amphoteric Character of Tris(pentafluoroethyl)silanide, [Si(C₂F₅)₃]⁻ (Angew. Chem. Int. Ed. 21/2021)

Natalia Tiessen, Mira Keßler, Beate Neumann, Hans‐Georg Stammler, more

Angewandte Chemie International Edition > 60 > 21 > 11533 - 11533

The tris(pentafluoroethyl)silanide anion adds to carbonyl compounds Ph(R)CO (R=Ph, H), CS₂, and CO₂, allowing the isolation of novel negatively charged species like [Si(C₂F₅)₃(η²‐OC(R)Ph)]⁻ (R=Ph, H), [Si(C₂F₅)₃(η²‐CS₂)]⁻, and [Si(C₂F₅)₃(η²‐CO₃)]⁻. Details of the reactions are described by Berthold Hoge et al. in their Research Article on page 12124.

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Titelbild: Nachweis des Lewis‐amphoteren Charakters von Tris(pentafluorethyl)silanid, [Si(C₂F₅)₃]⁻ (Angew. Chem. 21/2021)

Natalia Tiessen, Mira Keßler, Beate Neumann, Hans‐Georg Stammler, more

Angewandte Chemie > 133 > 21 > 11637 - 11637

Das Tris(pentafluorethyl)silanid‐Anion addiert an Carbonylverbindungen Ph(R)CO (R=Ph, H), CS₂ und CO₂, was die Isolierung neuartiger negativ geladener Spezies wie [Si(C₂F₅)₃(η²‐OC(R)Ph)]⁻ (R=Ph, H), [Si(C₂F₅)₃(η²‐CS₂)]⁻ und [Si(C₂F₅)₃(η²‐CO₃)]⁻ ermöglicht. Details zu den Reaktionen werden im Forschungsartikel von Berthold Hoge et al. auf S. 12231 beschrieben.

INFONA - science communication portal

Search results for: Berthold Hoge

First Main‐Group Element Lewis Acid Thionyl Chloride Adduct and its Chemistry

First Main‐Group Element Lewis Acid Thionyl Chloride Adduct and its Chemistry

Water‐Stable Lewis Superacids as Precursors for (Pseudo)halogenogallate and ‐indate Salts

Water Adducts of the Lewis Superacids: Tris(pentafluoroethyl)gallane and ‐indane

Gallate and Indate Salts with Unsaturated Electron Withdrawing Groups

Synthesis and Characterization of Tetrakis(pentafluoroethyl)indate Salts

Frontispiece: Oxidative Additions of C−F Bonds to the Silanide Anion [Si(C₂F₅)₃]⁻

Oxidative Additions of C−F Bonds to the Silanide Anion [Si(C₂F₅)₃]⁻

Frontispiz: Oxidative Addition von C−F‐Bindungen an das Silanid‐Anion [Si(C₂F₅)₃]⁻

Oxidative Addition von C−F‐Bindungen an das Silanid‐Anion [Si(C₂F₅)₃]⁻

Synthesis, Reactivity and Structural Properties of Trifluoromethylphosphoranides

Cover Feature: Tetrakis(pentafluoroethyl)gallate, [Ga(C₂F₅)₄]⁻, Ionic Liquids (Chem. Eur. J. 53/2021)

Tetrakis(pentafluoroethyl)gallate, [Ga(C₂F₅)₄]⁻, Ionic Liquids

Cover Feature: Tris(pentafluoroethyl)silanol Derivatives and the Lewis Amphoteric Tris(pentafluoroethyl)silanolate Anion, [Si(C₂F₅)₃O]⁻ (Chem. Eur. J. 43/2021)

Tris(pentafluoroethyl)silanol Derivatives and the Lewis Amphoteric Tris(pentafluoroethyl)silanolate Anion, [Si(C₂F₅)₃O]⁻

Phosphorus‐Containing Superbases: Recent Progress in the Chemistry of Electron‐Abundant Phosphines and Phosphazenes

Frontispiece: Phosphorus‐Containing Superbases: Recent Progress in the Chemistry of Electron‐Abundant Phosphines and Phosphazenes

Evidence of the Lewis‐Amphoteric Character of Tris(pentafluoroethyl)silanide, [Si(C₂F₅)₃]⁻

Cover Picture: Evidence of the Lewis‐Amphoteric Character of Tris(pentafluoroethyl)silanide, [Si(C₂F₅)₃]⁻ (Angew. Chem. Int. Ed. 21/2021)

Titelbild: Nachweis des Lewis‐amphoteren Charakters von Tris(pentafluorethyl)silanid, [Si(C₂F₅)₃]⁻ (Angew. Chem. 21/2021)

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