Tetraarylethylenes from Diarylmethanones and Hexachlorodisilane: The "Sila-McMurry" Reaction.
Hexachlorodisilane reacts with diarylmethanones (aryl=C6H5, 4-MeC6H4, 4-tBuC6H4, 4-ClC6H4, 4-BrC6H4) to furnish the corresponding tetraarylethylenes in good yields. The reductive conversion requires temperatures of about 160 °C and reaction times of 60-72 h. In the initial step, the Lewis-basic carbonyl groups likely generate low-valent [SiCl2] as an analogue of [TiCl2] in the classical McMurry reaction. The coupling sequence further proceeds via benzopinacolones, which have been isolated as key intermediates.
Institut für Anorganische Chemie, Goethe Universität Frankfurt, Max-von-Laue-Straße 7, 60438, Frankfurt am Main, Germany.
Maximilian
M
Moxter
Institut für Anorganische Chemie, Goethe Universität Frankfurt, Max-von-Laue-Straße 7, 60438, Frankfurt am Main, Germany.
Jan
J
Tillmann
Institut für Anorganische Chemie, Goethe Universität Frankfurt, Max-von-Laue-Straße 7, 60438, Frankfurt am Main, Germany.
Matthias
M
Füser
Institut für Anorganische Chemie, Goethe Universität Frankfurt, Max-von-Laue-Straße 7, 60438, Frankfurt am Main, Germany.
Michael
M
Bolte
Institut für Anorganische Chemie, Goethe Universität Frankfurt, Max-von-Laue-Straße 7, 60438, Frankfurt am Main, Germany.
Hans-Wolfram
HW
Lerner
Institut für Anorganische Chemie, Goethe Universität Frankfurt, Max-von-Laue-Straße 7, 60438, Frankfurt am Main, Germany. Matthias.Wagner@chemie.uni-frankfurt.de.
Matthias
M
Wagner
C−C coupling; Sila-McMurry reaction; alkenes; dichlorosilylene; reaction mechanism