Improved Synthesis of 1,2-Bis(trimethylsilyl)benzenes using Rieke-Magnesium or the Entrainment Method

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2010
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Reus, Christian
Bolte, Michael
Lerner, Hans-Wolfram
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Advanced Synthesis & Catalysis. 2010, 352(18), pp. 3443-3449. ISSN 1615-4150. eISSN 1615-4169. Available under: doi: 10.1002/adsc.201000560
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1,2-Bis(trimethylsilyl)benzene is the key starting material for the synthesis of efficient benzyne precursors and certain luminescent π-conjugated materials. We now report that it can be conveniently prepared in tetrahydrofuran from 1,2-dibromobenzene, chlorotrimethylsilane, and either Rieke-magnesium (MgR) or magnesium turnings in the presence of 1,2-dibromoethane as an entrainer (Mge). The most important advantages of these new protocols over the currently best-established procedure (1,2-dichlorobenzene, chlorotrimethylsilane, magnesium turnings, hexamethylphosphoramide) lie in the milder reaction conditions (MgR: 0 °C, 2 h; Mge: room temperature, 30 min vs. 100 °C, 2 days) and in the fact that the cancerogenic solvent hexamethylphosphoramide is avoided. Moreover, the improved protocols are also applicable for the high-yield synthesis of 1,2,4,5-tetrakis(trimethylsilyl)benzene, 4-fluoro-1,2-bis(trimethylsilyl)benzene, 4-chloro-1,2-bis(trimethylsilyl)benzene, and 4,5-dichloro-1,2-bis(trimethylsilyl)benzene.

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ISO 690LORBACH, Andreas, Christian REUS, Michael BOLTE, Hans-Wolfram LERNER, Matthias WAGNER, 2010. Improved Synthesis of 1,2-Bis(trimethylsilyl)benzenes using Rieke-Magnesium or the Entrainment Method. In: Advanced Synthesis & Catalysis. 2010, 352(18), pp. 3443-3449. ISSN 1615-4150. eISSN 1615-4169. Available under: doi: 10.1002/adsc.201000560
BibTex
@article{Lorbach2010-12-17Impro-39155,
  year={2010},
  doi={10.1002/adsc.201000560},
  title={Improved Synthesis of 1,2-Bis(trimethylsilyl)benzenes using Rieke-Magnesium or the Entrainment Method},
  number={18},
  volume={352},
  issn={1615-4150},
  journal={Advanced Synthesis & Catalysis},
  pages={3443--3449},
  author={Lorbach, Andreas and Reus, Christian and Bolte, Michael and Lerner, Hans-Wolfram and Wagner, Matthias}
}
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