chloro-trimethyl-silane; water; sodium iodide in acetonitrile 0.5 h; Ambient temperature;

chloro-trimethyl-silane; water; sodium iodide in acetonitrile 0.5 h; Ambient temperature;

sodium iodide in acetone Heating;

chloro-trimethyl-silane; water; sodium iodide in acetonitrile 0.5 h; Ambient temperature;

magnesium iodide in benzene T=80°C; 3 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

magnesium iodide in benzene T=80°C; 3 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

1: 96 percent / pyridine / CH2Cl2 / 12 h / Ambient temperature 2: 85 percent / NaI / acetone / Heating View Scheme

tin; chloro-trimethyl-silane; water; sodium iodide multistep reaction; other reagents, other aldehydes, other allylic alcohols; Mechanism;

1.1: n-Bu2SnO / methanol / 0.5 h / Heating 1.2: dimethylformamide / 8 h / 20 °C 2.1: PhSeOTf / tetrahydrofuran; CH2Cl2 / 3 h / -78 - 20 °C 2.2: aq. NaIO4; NaHCO3 / methanol / 5 h / 70 °C 3.1: dimethydioxirane / acetone / 2 h / 20 °C 4.1: PhSeSePH; NaBH4 / ethanol / 2 h / 60 °C 4.2: aq. NaIO4; NaHCO3 / methanol / 0.17 h / 20 °C 4.3: CCl4 / 12 h / 70 °C 5.1: n-BuLi / tetrahydrofuran / 0.08 h / -78 °C 5.2: 98 percent / tetrahydrofuran / 1 h / -78 °C 6.1: PhSeBr / acetonitrile / 24 h / 60 °C 6.2: aq. NaIO4; NaHCO3 / methanol / 0.17 h / 20 °C 6.3: methanol / 48 h / 70 °C 7.1: 60 percent / aq. OsO4; NMO / acetone / 48 h / 60 °C 8.1: 68 percent / H2; aq. HCl / Pd(OH)2 / ethanol / 24 h / 20 °C / 2585.74 Torr View Scheme

in acetonitrile 2 h; Heating;