Synthesis of Cyclic Alkyl(amino) Carbene Stabilized Silylenes with Small N-Donating Substituents

Wenling Li; Christian Köhler; Zhi Yang; Dietmar Stalke; Regine Herbst-Irmer; Herbert W. Roesky

doi:10.1002/chem.201805267

Synthesis of Cyclic Alkyl(amino) Carbene Stabilized Silylenes with Small N-Donating Substituents

Wenling Li, Christian Köhler, Zhi Yang^*, Dietmar Stalke, Regine Herbst-Irmer, Herbert W. Roesky

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Research output: Contribution to journal › Article › peer-review

7 Citations (Scopus)

Abstract

Lewis base cAACs stabilized monomeric silylenes with halogen or methyl substituents at the silicon center have not been reported due to the strong σ-donor and π-acceptor character of cAAC. To prepare these monomeric silylenes, we used the silicon(IV) precursors 5 and 6 with a nitrogen donor group L (L=o-C₆H₄NMe₂). The cAAC-stabilized (cAAC=C(CH₂)(CMe₂)₂N-Ar, Ar=2,6-iPr₂C₆H₃) silylenes LSiCl(cAAC) (7) and LSiMe(cAAC) (8) were synthesized by reduction of LSiCl₃ and LSiMeCl₂ with two equivalents of KC₈ in the presence of one equivalent of cAAC, respectively. Compounds 7 and 8 were characterized by single-crystal X-ray crystallography, NMR spectroscopy, and elemental analysis. Compounds 7 and 8 are stable in the solid state as well as in solution at room temperature for at least four months under inert conditions.

Original language	English
Pages (from-to)	1193-1197
Number of pages	5
Journal	Chemistry - A European Journal
Volume	25
Issue number	5
DOIs	https://doi.org/10.1002/chem.201805267
Publication status	Published - 24 Jan 2019

Keywords

Lewis bases
cAAC carbenes
side-arm donation
silylenes
single-crystal X-ray structure

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10.1002/chem.201805267

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title = "Synthesis of Cyclic Alkyl(amino) Carbene Stabilized Silylenes with Small N-Donating Substituents",

abstract = "Lewis base cAACs stabilized monomeric silylenes with halogen or methyl substituents at the silicon center have not been reported due to the strong σ-donor and π-acceptor character of cAAC. To prepare these monomeric silylenes, we used the silicon(IV) precursors 5 and 6 with a nitrogen donor group L (L=o-C6H4NMe2). The cAAC-stabilized (cAAC=C(CH2)(CMe2)2N-Ar, Ar=2,6-iPr2C6H3) silylenes LSiCl(cAAC) (7) and LSiMe(cAAC) (8) were synthesized by reduction of LSiCl3 and LSiMeCl2 with two equivalents of KC8 in the presence of one equivalent of cAAC, respectively. Compounds 7 and 8 were characterized by single-crystal X-ray crystallography, NMR spectroscopy, and elemental analysis. Compounds 7 and 8 are stable in the solid state as well as in solution at room temperature for at least four months under inert conditions.",

keywords = "Lewis bases, cAAC carbenes, side-arm donation, silylenes, single-crystal X-ray structure",

author = "Wenling Li and Christian K{\"o}hler and Zhi Yang and Dietmar Stalke and Regine Herbst-Irmer and Roesky, {Herbert W.}",

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T1 - Synthesis of Cyclic Alkyl(amino) Carbene Stabilized Silylenes with Small N-Donating Substituents

AU - Li, Wenling

AU - Köhler, Christian

AU - Yang, Zhi

AU - Stalke, Dietmar

AU - Herbst-Irmer, Regine

AU - Roesky, Herbert W.

PY - 2019/1/24

Y1 - 2019/1/24

N2 - Lewis base cAACs stabilized monomeric silylenes with halogen or methyl substituents at the silicon center have not been reported due to the strong σ-donor and π-acceptor character of cAAC. To prepare these monomeric silylenes, we used the silicon(IV) precursors 5 and 6 with a nitrogen donor group L (L=o-C6H4NMe2). The cAAC-stabilized (cAAC=C(CH2)(CMe2)2N-Ar, Ar=2,6-iPr2C6H3) silylenes LSiCl(cAAC) (7) and LSiMe(cAAC) (8) were synthesized by reduction of LSiCl3 and LSiMeCl2 with two equivalents of KC8 in the presence of one equivalent of cAAC, respectively. Compounds 7 and 8 were characterized by single-crystal X-ray crystallography, NMR spectroscopy, and elemental analysis. Compounds 7 and 8 are stable in the solid state as well as in solution at room temperature for at least four months under inert conditions.

AB - Lewis base cAACs stabilized monomeric silylenes with halogen or methyl substituents at the silicon center have not been reported due to the strong σ-donor and π-acceptor character of cAAC. To prepare these monomeric silylenes, we used the silicon(IV) precursors 5 and 6 with a nitrogen donor group L (L=o-C6H4NMe2). The cAAC-stabilized (cAAC=C(CH2)(CMe2)2N-Ar, Ar=2,6-iPr2C6H3) silylenes LSiCl(cAAC) (7) and LSiMe(cAAC) (8) were synthesized by reduction of LSiCl3 and LSiMeCl2 with two equivalents of KC8 in the presence of one equivalent of cAAC, respectively. Compounds 7 and 8 were characterized by single-crystal X-ray crystallography, NMR spectroscopy, and elemental analysis. Compounds 7 and 8 are stable in the solid state as well as in solution at room temperature for at least four months under inert conditions.

KW - Lewis bases

KW - cAAC carbenes

KW - side-arm donation

KW - silylenes

KW - single-crystal X-ray structure

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Synthesis of Cyclic Alkyl(amino) Carbene Stabilized Silylenes with Small N-Donating Substituents

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