Reductive coupling of carbonyl compounds with zinc and trimethylchlorosilane to produce O-silylated pinacols. Effect of ultrasonic waves

JH So, MK Park, P Boudjouk

Index: So, Jeung-Ho; Park, Moon-Kyeu; Boudjouk, Philip Journal of Organic Chemistry, 1988 , vol. 53, # 25 p. 5871 - 5875

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Citation Number: 44

Abstract

Trimethylchlorosilane reacts with carbonyl compounds in the presence of zinc to give 0- 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. Crowcoupling reactions yield ...