Abstract
Hexaarylcyclotrisiloxane, which is one of the most stable derivatives of diarylsilanediol, was found to undergo palladium-catalyzed cross-coupling reaction with aryl halides in good yields. The reaction is performed in an aqueous medium taking potassium hydroxide as an activator. Both of the two aryl groups attached to each silicon atom could be utilized. Some base-sensitive functionality such as acetyl and nitro groups survived the reaction.
Key words
silicon - cross-coupling - palladium - halides - biaryls
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Typical Reaction Procedure.
1a , 59.5 mg, 0.10 mmol) was added to a solution composed of aq KOH solution (3.0 mol dm-3 , 1.4 mL, 4.2 mmol) and H2 O (0.6 mL) under an argon atmosphere. The mixture was heated to reflux for 1 h. Then, 4-iodoanisole (2b ; 112 mg, 0.48 mmol) and Pd(OAc)2 (5.4 mg, 0.024 mmol) were added to the resulting solution, successively. The yellow solution was heated under reflux for 4 h. After the mixture was cooled to r.t. and was extracted with CH2 Cl2 (3 × 20 mL). The combined organic layer was dried over anhyd Na2 SO4 . Silica gel column chromatography after concentration afforded 3a (80.2 mg, 91%).
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