tetrakis(triphenylphosphine) palladium(0); sodium methylate in N,N-dimethyl-formamide T=20°C; Suzuki-Miyaura cross coupling reaction; 3 h; Inert atmosphere;

1: 96 percent / toluene / 6 h / Heating 2: 1. NaH / diethyl ether / 1.) two days, ultrasonic bath, 2.) 10-15 min. View Scheme

sodium hydride in diethyl ether 1.) two days, ultrasonic bath, 2.) 10-15 min.; Yield given;

1: para-iodobenzonitrile With tBu4ZnLi2 in tetrahydrofuran T=0°C; Inert atmosphere; 2: propargyl bromide in tetrahydrofuran T=-78 - 20°C; Inert atmosphere; regioselective reaction;