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Open AccessArticle

Synthesis and Characterization of N-Heterocyclic Carbene-Coordinated Silicon Compounds Bearing a Fused-Ring Bulky Eind Group

1
Department of Applied Chemistry, Faculty of Science and Engineering, Kindai University 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, Japan
2
Institute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto 611-0011, Japan
3
Department of Biomolecular Functional Engineering, College of Engineering, Ibaraki University, 4-12-1 Nakanarusawa, Hitachi, Ibaraki 316-8511, Japan
4
Graduate School of Natural Sciences, Nagoya City University Yamanohata 1, Mizuho-cho, Mizuho-ku, Nagoya, Aichi 467-8501, Japan
5
RIKEN Center for Emergent Matter Science (CEMS), 2-1 Hirosawa, Wako, Saitama 351-0198, Japan
*
Author to whom correspondence should be addressed.
Inorganics 2018, 6(1), 30; https://doi.org/10.3390/inorganics6010030
Received: 23 December 2017 / Revised: 13 February 2018 / Accepted: 14 February 2018 / Published: 23 February 2018
(This article belongs to the Special Issue Coordination Chemistry of Silicon)
The reactions of the fused-ring bulky Eind-substituted 1,2-dibromodisilene, (Eind)BrSi=SiBr(Eind) (1a) (Eind = 1,1,3,3,5,5,7,7-octaethyl-s-hydrindacen-4-yl (a)), with N-heterocyclic carbenes (NHCs) (Im-Me4 = 1,3,4,5-tetramethylimidazol-2-ylidene and Im-iPr2Me2 = 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene) are reported. While the reaction of 1a with the sterically more demanding Im-iPr2Me2 led to the formation of the mono-NHC adduct of arylbromosilylene, (Im-iPr2Me2)→SiBr(Eind) (2a′), a similar reaction using the less bulky Im-Me4 affords the bis-NHC adduct of formal arylsilyliumylidene cation, [(Im-Me4)2→Si(Eind)]+[Br] (3a). The NHC adducts 2a′ and 3a can also be prepared by the dehydrobromination of Eind-substituted dibromohydrosilane, (Eind)SiHBr2 (4a), with NHCs. The NHC-coordinated silicon compounds have been characterized by spectroscopic methods. The molecular structures of bis-NHC adduct, [(Im-iPr2Me2)2→Si(Eind)]+[Br] (3a′), and 4a have been determined by X-ray crystallography. View Full-Text
Keywords: silicon; N-heterocyclic carbenes; bromosilylenes; silyliumylidenes; dehydrobromination silicon; N-heterocyclic carbenes; bromosilylenes; silyliumylidenes; dehydrobromination
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Hayakawa, N.; Sadamori, K.; Mizutani, S.; Agou, T.; Sugahara, T.; Sasamori, T.; Tokitoh, N.; Hashizume, D.; Matsuo, T. Synthesis and Characterization of N-Heterocyclic Carbene-Coordinated Silicon Compounds Bearing a Fused-Ring Bulky Eind Group. Inorganics 2018, 6, 30.

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