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

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

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LORBACH, 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. 352(18), pp. 3443-3449. ISSN 1615-4150. eISSN 1615-4169. Available under: doi: 10.1002/adsc.201000560

@article{Lorbach2010-12-17Impro-39155, title={Improved Synthesis of 1,2-Bis(trimethylsilyl)benzenes using Rieke-Magnesium or the Entrainment Method}, year={2010}, doi={10.1002/adsc.201000560}, 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} }

Improved Synthesis of 1,2-Bis(trimethylsilyl)benzenes using Rieke-Magnesium or the Entrainment Method 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 (Mg<sup>R</sup>) or magnesium turnings in the presence of 1,2-dibromoethane as an entrainer (Mg<sup>e</sup>). 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 (Mg<sup>R</sup>: 0 °C, 2 h; Mg<sup>e</sup>: 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. Lorbach, Andreas 2017-06-07T09:52:46Z 2010-12-17 Bolte, Michael Lorbach, Andreas eng 2017-06-07T09:52:46Z Wagner, Matthias Wagner, Matthias Lerner, Hans-Wolfram Reus, Christian terms-of-use Lerner, Hans-Wolfram Reus, Christian Bolte, Michael

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