Synthesis of a Silylium Zwitterion

Ramírez-Contreras, Rodrigo; Bhuvanesh, Nattamai; Zhou, Jia; Ozerov, Oleg V.

doi:10.1002/ange.201302082

Angewandte Chemie

2013

DOI: 10.1002/ange.201302082

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Synthesis of a Silylium Zwitterion

Rodrigo Ramírez-Contreras

Nattamai Bhuvanesh

Jia Zhou

et al.

Abstract: Positiv und negativ zugleich: In einem neuen Zwitterion sind ein Trialkylsilyliumkation und ein schwach koordinierendes Carborananion in einem einzigen neutralen Molekül kovalent miteinander verknüpft (siehe Röntgenkristallstruktur; Si grün, C grau, B orange, Cl rot). Der Silyliumcharakter dieses Moleküls wird durch DFT‐Rechnungen (siehe LUMO), 29Si‐CP/MAS‐NMR‐Spektroskopie und seine Reaktivität gestützt.

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Cited by 7 publications

References 35 publications

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Fusing N‐Heterocyclic Carbenes with Carborane Anions

El‐Hellani

Lavallo

2014

Angewandte Chemie

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Here we describe the fusion of two families of unusual carbon-containing molecules that readily disregard the tendency of carbon to form four chemical bonds, namely Nheterocyclic carbenes (NHCs) and carborane anions. Deprotonation of an anionic imidazolium salt with lithium diisopropylamide at room temperature leads to a mixture of lithium complexes of C-2 and C-5 dianionic NHC constitutional isomers as well as a trianionic (C-2, C-5) adduct. Judicious choice of the base and reaction conditions allows the selective formation of all three stable polyanionic carbenes. In solution, the so-called abnormal C-5 NHC lithium complex slowly isomerizes to the normal C-2 NHC, and the process can be proton-catalyzed by the addition of the anionic imidazolium salt. These results indicate that the combination of two unusual forms of carbon atoms can lead to unexpected chemical behavior, and that this strategy paves the way for the development of a broad new generation of NHC ligands for catalysis.

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Fusing N‐Heterocyclic Carbenes with Carborane Anions

El‐Hellani

Lavallo

2014

Angewandte Chemie

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“Dumbbell”‐ and “Clackers”‐Shaped Dimeric Derivatives of Monocarba‐closo‐dodecaborate

et al. 2018

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We designed, synthesized, and characterized two types of dimeric forms of monocarba-closo-dodecaborate, namely,a"dumbbell"-shaped dianion having aC ÀCbond and a" clackers"-shaped monoanion having an iodonium linker. The unique architectures of these anionic molecules were established by X-ray analysis.S pectroscopic analysis,D FT calculations,a nd reactivity experiments revealed high anionic and chemical stability of both anions,w hich are crucial properties for weakly coordinating anions.

show abstract

Fusing N‐Heterocyclic Carbenes with Carborane Anions

2014

View full text Add to dashboard Cite

Here we describe the fusion of two families of unusual carbon-containing molecules that readily disregard the tendency of carbon to form four chemical bonds, namely N-heterocyclic carbenes (NHCs) and carborane anions. Deprotonation of an anionic imidazolium salt with lithium diisopropylamide at room temperature leads to a mixture of lithium complexes of C-2 and C-5 dianionic NHC constitutional isomers as well as a trianionic (C-2, C-5) adduct. Judicious choice of the base and reaction conditions allows the selective formation of all three stable polyanionic carbenes. In solution, the so-called abnormal C-5 NHC lithium complex slowly isomerizes to the normal C-2 NHC, and the process can be proton-catalyzed by the addition of the anionic imidazolium salt. These results indicate that the combination of two unusual forms of carbon atoms can lead to unexpected chemical behavior, and that this strategy paves the way for the development of a broad new generation of NHC ligands for catalysis.

show abstract

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Synthesis of a Silylium Zwitterion

Cited by 7 publications

References 35 publications

Fusing N‐Heterocyclic Carbenes with Carborane Anions

Fusing N‐Heterocyclic Carbenes with Carborane Anions

“Dumbbell”‐ and “Clackers”‐Shaped Dimeric Derivatives of Monocarba‐closo‐dodecaborate

Fusing N‐Heterocyclic Carbenes with Carborane Anions

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