Palladium??Catalyzed Cyclopropanation of Alkenyl Silanes by Diazoalkanes: Evidence for a Pd0 Mechanism

G Berthon??Gelloz, M Marchant…

Index: Berthon-Gelloz, Guillaume; Marchant, Melanie; Straub, Bernd F.; Marko, Istvan E. Chemistry - A European Journal, 2009 , vol. 15, # 12 p. 2923 - 2931

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Citation Number: 14

Abstract

Alkenyl silanes are efficiently converted to the corresponding silyl cyclopropanes in the presence of a slight excess of diazomethane (2–4 equiv) and a low loading of Pd(OAc) 2 (<0.5 mol %). Diazoethane and diazobutane can also be employed and yield silyl cyclopropanes with diastereoselectivities of up to 10:1 for the trans isomer. When conducted on a 4 g scale, the reaction only required a catalyst loading of 5×10 −3 mol %, which corresponds to a turnover frequency of 40 000 ...