- A convenient iron-catalyzed method for the preparation of 1,2-bis(trimethylsilyl)benzenes
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A convenient iron-catalyzed method for the preparation of 1,2-bis(trimethylsilyl)benzenes is presented. Compared to the current procedures, low temperatures and toxic solvents are avoided, allowing large-scale preparation. Additionally, a variety of subst
- Bader, Samuel L.,Kessler, Simon N.,Wegner, Hermann A.
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experimental part
p. 2759 - 2762
(2010/10/05)
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- Improved synthesis of 1,2-bis(trimethylsilyl)benzenes using Rieke-magnesium or the entrainment method
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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. Copyright
- Lorbach, Andreas,Reus, Christian,Bolte, Michael,Lerner, Hans-Wolfram,Wagner, Matthias
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supporting information; experimental part
p. 3443 - 3449
(2011/02/24)
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