tetrakis(triphenylphosphine) palladium(0); sodium carbonate in ethylene glycol dimethyl ether

1.1: 91 percent / 3-chloroperoxybenzoic acid / CH2Cl2 / 2 h / 20 °C 2.1: 82 percent / stannous chloride; hydrochloric acid / ethanol / 6 h / Heating 3.1: sodium nitrite; hydrochloric acid / H2O / 0.25 h / -5 °C 3.2: 89 percent / potassium iodide / H2O; CH2Cl2 / 4 h / 20 °C 4.1: 10 percent / tributyltin hydride; 2,2'-diazobisisobutyronitrile / 12 h / Heating View Scheme

1.1: sodium nitrite; hydrochloric acid / H2O / 0.25 h / -5 °C 1.2: 89 percent / potassium iodide / H2O; CH2Cl2 / 4 h / 20 °C 2.1: 10 percent / tributyltin hydride; 2,2'-diazobisisobutyronitrile / 12 h / Heating View Scheme

1.1: 82 percent / stannous chloride; hydrochloric acid / ethanol / 6 h / Heating 2.1: sodium nitrite; hydrochloric acid / H2O / 0.25 h / -5 °C 2.2: 89 percent / potassium iodide / H2O; CH2Cl2 / 4 h / 20 °C 3.1: 10 percent / tributyltin hydride; 2,2'-diazobisisobutyronitrile / 12 h / Heating View Scheme

1.1: 79 percent / triphenylphosphine; Pd2(dba)3; potassium tert-butoxide / ethanol / 8 h / Heating 2.1: 91 percent / 3-chloroperoxybenzoic acid / CH2Cl2 / 2 h / 20 °C 3.1: 82 percent / stannous chloride; hydrochloric acid / ethanol / 6 h / Heating 4.1: sodium nitrite; hydrochloric acid / H2O / 0.25 h / -5 °C 4.2: 89 percent / potassium iodide / H2O; CH2Cl2 / 4 h / 20 °C 5.1: 10 percent / tributyltin hydride; 2,2'-diazobisisobutyronitrile / 12 h / Heating View Scheme

1.1: sodium nitrite; hydrochloric acid / H2O / 0.5 h / -5 °C 1.2: 56 percent / potassium iodide / H2O / 2 h / Heating 2.1: 79 percent / triphenylphosphine; Pd2(dba)3; potassium tert-butoxide / ethanol / 8 h / Heating 3.1: 91 percent / 3-chloroperoxybenzoic acid / CH2Cl2 / 2 h / 20 °C 4.1: 82 percent / stannous chloride; hydrochloric acid / ethanol / 6 h / Heating 5.1: sodium nitrite; hydrochloric acid / H2O / 0.25 h / -5 °C 5.2: 89 percent / potassium iodide / H2O; CH2Cl2 / 4 h / 20 °C 6.1: 10 percent / tributyltin hydride; 2,2'-diazobisisobutyronitrile / 12 h / Heating View Scheme

1: NaN3 2: Irradiation View Scheme

2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride 12 h; Heating;

Irradiation;