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Inorganics 2018, 6(1), 30; https://doi.org/10.3390/inorganics6010030

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.
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)
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Abstract

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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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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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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