triethylsilane; trifluoroacetic acid in dichloromethane T=20°C; 4 h;

sodium sulfate in 1,4-dioxane; water 1.) 0 deg C, 3 h; 2.) 20 deg C, 16 h;

1.1: 78 percent / aq. NaHCO3 / acetone / 48 h / 20 °C 2.1: 84 percent / H2SO4 / CH2Cl2 / 19 h / 20 °C 3.1: 99 percent / NaI / acetone / 72 h / Heating 4.1: Zn; Me3SiCl / dimethylformamide / 20 °C 4.2: 34 percent / P(o-tol)3 / tris(dibenzylideneacetone)dipalladium / dimethylformamide / 4 h / 50 °C 5.1: 64 percent / Et3SiH; TFA / CH2Cl2 / 4 h / 20 °C View Scheme

1.1: Zn; Me3SiCl / dimethylformamide / 20 °C 1.2: 34 percent / P(o-tol)3 / tris(dibenzylideneacetone)dipalladium / dimethylformamide / 4 h / 50 °C 2.1: 64 percent / Et3SiH; TFA / CH2Cl2 / 4 h / 20 °C View Scheme

1.1: 84 percent / H2SO4 / CH2Cl2 / 19 h / 20 °C 2.1: 99 percent / NaI / acetone / 72 h / Heating 3.1: Zn; Me3SiCl / dimethylformamide / 20 °C 3.2: 34 percent / P(o-tol)3 / tris(dibenzylideneacetone)dipalladium / dimethylformamide / 4 h / 50 °C 4.1: 64 percent / Et3SiH; TFA / CH2Cl2 / 4 h / 20 °C View Scheme

1.1: 99 percent / NaI / acetone / 72 h / Heating 2.1: Zn; Me3SiCl / dimethylformamide / 20 °C 2.2: 34 percent / P(o-tol)3 / tris(dibenzylideneacetone)dipalladium / dimethylformamide / 4 h / 50 °C 3.1: 64 percent / Et3SiH; TFA / CH2Cl2 / 4 h / 20 °C View Scheme