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Copper(I) tert-butoxide-promoted coupling of arylsilanes possessing a 1-hydroxyalkyl group at the o-position with organic halides proceeded to give disubstituted arenes. The results indicate that an intermediary arylcopper species is formed by aromatic Csp2-to-O silyl migration.
Treatment of rubrene (5,6,11,12-tetraphenylnaphthacene) with trifluoroacetic acid in dichloromethane gives 4b,9,10-triphenyl-4b,9-dihydroindeno[1,2,3-fg]naphthacene (1) as the sole isolable product. Paired interacting orbital (PIO) analysis indicates that the reaction is initiated by preferential attack of H + at C(11) position of rubrene.
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