Synthesis of a Base‐Stabilized 1‐Hydrosilanimine via NHC‐Mediated Dehydrohalogenation of Hydrochlorosilane

Cui, Haiyan; Cui, Chunming

doi:10.1002/asia.201100022

Cited by 36 publications

(28 citation statements)

References 43 publications

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“…Pertinent metric parameters are collected in Table . The silicon bond lengths and angles compare well with those determined for closely related diaminochlorosilanes …”

Section: Resultssupporting

confidence: 61%

On the Way to N‐Heterocyclic Silylenes with a 1,1′‐Ferrocenediyl Backbone: Synthesis and Structures of Silicon(IV) Compounds of the Type [Fe{(η⁵‐C₅H₄)NR}₂SiX₂]

Oetzel

Bruhn

Siemeling

2018

Zeitschrift anorg allge chemie

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Potential precursors for the synthesis of ferrocene-based Nheterocyclic silylenes of the type [Fe{(η 5 -C 5 H 4 )NR} 2 Si:] (1Si) were investigated. The silicon(IV) dibromides 1aSiBr 2 -1cSiBr 2 [a: R = SiMe 3 , b: R = CH 2 CMe 3 , c: R = 3,5-(CF 3 ) 2 -C 6 H 3 ] as well as the dichlorides 1aSiCl 2 and 1bSiCl 2 were prepared in high yield. Attempts to synthesize the target silylenes from these silicon(IV) dihalides by reductive methods failed. Strong reducing agent like alkali metals or KC 8 only afforded intractable mixtures. No reaction was observed with * Prof. Dr. U. Siemeling

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“…Pertinent metric parameters are collected in Table . The silicon bond lengths and angles compare well with those determined for closely related diaminochlorosilanes …”

Section: Resultssupporting

confidence: 61%

On the Way to N‐Heterocyclic Silylenes with a 1,1′‐Ferrocenediyl Backbone: Synthesis and Structures of Silicon(IV) Compounds of the Type [Fe{(η⁵‐C₅H₄)NR}₂SiX₂]

Oetzel

Bruhn

Siemeling

2018

Zeitschrift anorg allge chemie

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“…In addition, unsaturated compounds such as isonitriles and acetylenes reacted with NHC‐coordinated amidochloro‐substituted silylenes to yield silaimines ,. Furthermore, the addition of NHCs to amido‐substituted hydrochlorosilanes gave access to silaimines under release of an imidazolium salt . A Si‐metalated silaimine was recently synthesized from {N(SiMe 3 )Dipp}ClSi:→Ni(NHC i Pr2Me2 ) 2 as the precursor using N 2 O in a rearrangement cascade .…”

Section: Figurementioning

confidence: 99%

Facile Access to an NHC‐Coordinated Silicon Ring Compound with a Si=N Group and a Two‐Coordinate Silicon Atom

et al. 2019

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Reaction of the bicyclo[1.1.0]tetrasilatetraamide Si4{N(SiMe3)Dipp}4 1 (Dipp=2,6‐diisopropylphenyl) with 5 equiv of the N‐heterocyclic carbene NHCMe4 (1,3,4,5‐tetramethylimidazol‐2‐ylidene) affords a bifunctional carbene‐coordinated four‐membered‐ring compound with a Si=N group and a two‐coordinate silicon atom Si4{N(SiMe3)Dipp}2(NHCMe4)2(NDipp) 2. When 2 reacts with 0.25 equiv sulfur (S8), two sulfur atoms add to the divalent silicon atom in plane and perpendicular to the plane of the Si4 ring, which confirms the silylone character of the two‐coordinate silicon atom in 2.

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“…Compound 1 was synthesized from the reaction of dichlorosilane ArN(SiMe 3 )SiHCl 2 and I i Pr. [6a] However, the reaction of ArN(SiMe 3 )SiHCl 2 with less‐hindered carbene IMe 4 did not give the corresponding silylene . Interestingly, treatment of 1 with IMe 4 in C 6 D 6 at room temperature resulted in the rapid formation of a new species 4 and free I i Pr (Scheme ) as indicated by NMR spectroscopic analysis.…”

Section: Resultsmentioning

confidence: 99%

“…[6a] However, the reaction of ArN(SiMe 3 )SiHCl 2 with less-hindered carbene IMe 4 did not give the corresponding silylene. [18] Interestingly, treatment of 1 with IMe 4 in C 6 D 6 at room temperature resulted in the rapid formation of a new species 4 and free IiPr (Scheme 2) as indicated by NMR spectroscopic analysis. The reaction proceeded quantitatively, and compound 4 was obtained as pale yellow powder.…”

Section: Reaction Of Nhc-stabilized Silylene 1 With Nhcsmentioning

confidence: 96%

Reactivity of an NHC‐Stabilized Silylene towards Lewis Acids and Lewis Bases

Cui

Teng

2016

Eur J Inorg Chem

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The reactivity of N‐heterocyclic carbene stabilized (NHC‐stabilized) aminochlorosilylene ArN(SiMe3)Si(IiPr)Cl (1, Ar = 2,6‐iPr2C6H3, IiPr = 1,3‐diisopropyl‐4,5‐dimethylimidazol‐2‐ylidene) with selected Lewis acids and Lewis bases is described. Treatment of 1 with BH3·THF yielded 1·BH3 (2) quantitatively. Compound 2 is a rare example of an air‐insensitive silylene–borane adduct showing both acidic and basic properties of chlorosilylene in a single molecule. Crystals of 1–(CH2)3CH2OB(C6F5)3 (3) were obtained from the reaction of 1 with B(C6F5)3 in THF. For the first time, a frustrated Lewis pair (FLP) composed of a silylene and a substituted borane was observed to activate small molecules. Reaction of 1 with IMe4 (IMe4 = 1,3,4,5‐tetramethylimidazol‐2‐ylidene) at room temperature afforded silylene ArN(SiMe3)Si(IMe4)Cl (4), which represents a rare example of an NHC‐stabilized silylene synthesized through ligand exchange.

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Synthesis of a Base‐Stabilized 1‐Hydrosilanimine via NHC‐Mediated Dehydrohalogenation of Hydrochlorosilane

Cited by 36 publications

References 43 publications

On the Way to N‐Heterocyclic Silylenes with a 1,1′‐Ferrocenediyl Backbone: Synthesis and Structures of Silicon(IV) Compounds of the Type [Fe{(η⁵‐C₅H₄)NR}₂SiX₂]

On the Way to N‐Heterocyclic Silylenes with a 1,1′‐Ferrocenediyl Backbone: Synthesis and Structures of Silicon(IV) Compounds of the Type [Fe{(η⁵‐C₅H₄)NR}₂SiX₂]

Facile Access to an NHC‐Coordinated Silicon Ring Compound with a Si=N Group and a Two‐Coordinate Silicon Atom

Reactivity of an NHC‐Stabilized Silylene towards Lewis Acids and Lewis Bases

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Synthesis of a Base‐Stabilized 1‐Hydrosilanimine via NHC‐Mediated Dehydrohalogenation of Hydrochlorosilane

Cited by 36 publications

References 43 publications

On the Way to N‐Heterocyclic Silylenes with a 1,1′‐Ferrocenediyl Backbone: Synthesis and Structures of Silicon(IV) Compounds of the Type [Fe{(η5‐C5H4)NR}2SiX2]

On the Way to N‐Heterocyclic Silylenes with a 1,1′‐Ferrocenediyl Backbone: Synthesis and Structures of Silicon(IV) Compounds of the Type [Fe{(η5‐C5H4)NR}2SiX2]

Facile Access to an NHC‐Coordinated Silicon Ring Compound with a Si=N Group and a Two‐Coordinate Silicon Atom

Reactivity of an NHC‐Stabilized Silylene towards Lewis Acids and Lewis Bases

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On the Way to N‐Heterocyclic Silylenes with a 1,1′‐Ferrocenediyl Backbone: Synthesis and Structures of Silicon(IV) Compounds of the Type [Fe{(η⁵‐C₅H₄)NR}₂SiX₂]

On the Way to N‐Heterocyclic Silylenes with a 1,1′‐Ferrocenediyl Backbone: Synthesis and Structures of Silicon(IV) Compounds of the Type [Fe{(η⁵‐C₅H₄)NR}₂SiX₂]