copper(l) iodide; potassium carbonate; triphenylphosphine; palladium on activated charcoal in ethylene glycol dimethyl ether; water

1: 1.) lithium bis(trimethylsilyl)amide / 1) THF, -22 deg C, 0.5 h; 2) THF, tert-butyl methyl ether, -22 to 25 deg C, 25 deg C, 18 h 2: 71 percent / aq. HCl, charcoal / 1) 25 --> 98 deg C, 2 h; 2) 98 deg C, 2 h 3: 90 percent / sodium borohydride / methanol; acetic acid / 1) below -40 deg C, 1 h; 2) -40 deg C, 3 h; 3) 0 deg C, 18 h 4: 92 percent / formic acid / H2O / 18 h / 80 °C 5: 1.) K2CO3, copper(I) iodide, Ph3P / 1.) Pd/C / 1) DME, water, 25 deg C, 0.5 h; 2) DME, water, reflux, 16 h View Scheme

1: 92 percent / formic acid / H2O / 18 h / 80 °C 2: 1.) K2CO3, copper(I) iodide, Ph3P / 1.) Pd/C / 1) DME, water, 25 deg C, 0.5 h; 2) DME, water, reflux, 16 h View Scheme

1: 90 percent / sodium borohydride / methanol; acetic acid / 1) below -40 deg C, 1 h; 2) -40 deg C, 3 h; 3) 0 deg C, 18 h 2: 92 percent / formic acid / H2O / 18 h / 80 °C 3: 1.) K2CO3, copper(I) iodide, Ph3P / 1.) Pd/C / 1) DME, water, 25 deg C, 0.5 h; 2) DME, water, reflux, 16 h View Scheme

1: 71 percent / aq. HCl, charcoal / 1) 25 --> 98 deg C, 2 h; 2) 98 deg C, 2 h 2: 90 percent / sodium borohydride / methanol; acetic acid / 1) below -40 deg C, 1 h; 2) -40 deg C, 3 h; 3) 0 deg C, 18 h 3: 92 percent / formic acid / H2O / 18 h / 80 °C 4: 1.) K2CO3, copper(I) iodide, Ph3P / 1.) Pd/C / 1) DME, water, 25 deg C, 0.5 h; 2) DME, water, reflux, 16 h View Scheme