Abstract

Trimethylchlorosilane reacts with carbonyl compounds in the presence of zinc to give O-silylated pinacols, vicinal bis(trimethylsiloxy)alkanes, in good yields via reductive dimerization. This is a very mild route to bis(siloxy)alkanes, which are easily converted to pinacols or pinacolones in excellent yields. Electron-donating groups accelerate coupling while electron-withdrawing groups have an inhibiting effect. Cross-coupling reactions yield a mixture of bis(siloxy)alkanes

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