1: C16H13NOS2 With (2,2,6,6-tetramethylpiperidine)2Zn·2MgCl2·2LiCl in tetrahydrofuran T=25°C; 2 h; Inert atmosphere; 2: para-iodoanisole With Pd((1E,4E)-1,5-diphenylpenta-1,4-dien-3-one)2; trifuran-2-yl-phosphane in tetrahydrofuran T=25°C; Negishi coupling reaction; 3 h; Inert atmosphere;

sodium in ethanol Heating;

1: 61 percent / ethanol / 3 h / 60 °C 2: 53 percent / Na / ethanol / Heating View Scheme

1: 77.5 percent / Br2 / CCl4 / 0.5 h / 30 °C 2: 61 percent / ethanol / 3 h / 60 °C 3: 53 percent / Na / ethanol / Heating View Scheme

1.1: isopropylmagnesium chloride lithium chloride complex / tetrahydrofuran / 0.5 h / -40 °C / Inert atmosphere 1.2: 0.5 h / -40 °C / Inert atmosphere 2.1: (2,2,6,6-tetramethylpiperidine)2Zn·2MgCl2·2LiCl / tetrahydrofuran / 2 h / 25 °C / Inert atmosphere 2.2: 3 h / 25 °C / Inert atmosphere 3.1: (2,2,6,6-tetramethylpiperidine)2Zn·2MgCl2·2LiCl / tetrahydrofuran / 2 h / 25 °C / Inert atmosphere 3.2: 3 h / 25 °C / Inert atmosphere View Scheme