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• W2007202081 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 5x10(-3) mol %, which corresponds to a turnover frequency of 40,000 h(-1). Competition experiments revealed that vinyl silanes can be selectively cyclopropanated in the presence of an aliphatic terminal alkene and styrene. The complex [Pd(0) (2)(DVTMS)(3)] (38, DVTMS = divinyltetramethyldisiloxane) proved to be an exceptionally active catalyst for the cyclopropanation reaction, giving complete conversion at -35 degrees C in 1 min. Intermolecular and intramolecular competition experiments with DVTMS (36), both with Pd(OAc)(2) and 38, provided strong evidence for a Pd(0)(alkenyl silane)(3) resting state. Detailed density functional calculations on the reaction pathways for the cyclopropanation of trimethylvinylsilane and DVTMS by diazomethane with Pd(0) corroborated the experimental observations." @default.
• W2007202081 created "2016-06-24" @default.
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• W2007202081 date "2009-03-09" @default.
• W2007202081 modified "2023-10-18" @default.
• W2007202081 title "Palladium-Catalyzed Cyclopropanation of Alkenyl Silanes by Diazoalkanes: Evidence for a Pd⁰Mechanism" @default.
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• W2007202081 doi "https://doi.org/10.1002/chem.200802052" @default.
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