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Bis(arylsilyl)arenes such as bis(p-tolylsilyl)benzene and bis(p-anisylsilyl)naphthalene are available from in situ Grignard reactions of the corresponding haloarenes, arylchlorosilanes and magnesium in tetrahydrofuran. Treatment of these products with one equivalent of trifluoromethanesulfonic (triflic) acid at low temperatures leads to arylsilyl(trifluoromethylsulfonatosilyl) arenes, which can be converted into arylsilyl(silyl)arenes using LiAlH 4 . The regioselectivity of the Si - C cleavage is surprisingly high. Any of the first dearylation steps is faster then the consecutive steps. Ortho, meta and para substituted p-tolylsilyl(silyl)benzenes, 1,4-dibromo-2-(p-tolylsilyl)-5-(silyl)benzene, and 1-(p-anisylsilyl)-8-(silyl)naphthalene have thus been obtained in good to moderate yields. These compounds can serve as starting materials for monofunctional arylsilanes with a tailored structure. The crystal structure of 1-(p-anisylsiIyI)-8-(siIyl)naphthalene has been determined by single crystal X-ray diffraction.

A Synthetic Pathway to Arylsilyl(silyl)arenes; Selective Si-C Cleavage in Bis(arylsilyl)arenes with Triflic Acid