tetrakis(triphenylphosphine) palladium(0) in 1,4-dioxane Heating;

tetrakis(triphenylphosphine) palladium(0) in 1,4-dioxane Heating;

copper(II) oxide in acetone 1 h; Heating;

tetrakis(triphenylphosphine) palladium(0) in 1,4-dioxane T=60°C; 3 h;

Celite; silver carbonate in benzene 3 h; Heating; Yield given;

1: 1.) 3-(5-nitro-2-oxo-1,2-dihydro-1-pyridyl)-1,2-benzisothiazole 1,1-dioxide (BID-NPy), triethylamine (TEA) / 1.) CH2Cl2, 0 deg C, 1.5 h, 2.) CH2Cl2, RT, 30 min 2: 1.) BuLi / 1.) THF, -78 to -20 deg C, 2 h, 2.) THF, RT, overnight 3: 1.) LDA / 1.) THF, -78 deg C to RT, 3 h, 2.) THF, RT, overnight 4: p-toluenesulfonic acid (PTSA), boric acid / toluene / 0.5 h / Heating 5: 89 percent / CuCl2*2H2O, CuO / acetone / 1 h / Heating View Scheme

1: 1.) BuLi / 1.) THF, -78 to -20 deg C, 2 h, 2.) THF, RT, overnight 2: 1.) LDA / 1.) THF, -78 deg C to RT, 3 h, 2.) THF, RT, overnight 3: p-toluenesulfonic acid (PTSA), boric acid / toluene / 0.5 h / Heating 4: 89 percent / CuCl2*2H2O, CuO / acetone / 1 h / Heating View Scheme

1: 1.) LDA / 1.) THF, -78 deg C to RT, 3 h, 2.) THF, RT, overnight 2: p-toluenesulfonic acid (PTSA), boric acid / toluene / 1 h / Heating 3: 89 percent / CuCl2*2H2O, CuO / acetone / 1 h / Heating View Scheme

1: 1.) LDA / 1.) THF, -78 deg C to RT, 3 h, 2.) THF, RT, overnight 2: p-toluenesulfonic acid (PTSA), boric acid / toluene / 0.5 h / Heating 3: 89 percent / CuCl2*2H2O, CuO / acetone / 1 h / Heating View Scheme