1: (4-methoxymethoxy)phenylphenylacetylene With Me3SnLi in tetrahydrofuran; hexane T=0°C; 3 h; Inert atmosphere; 2: With zinc(II) chloride in tetrahydrofuran; hexane T=0 - 20°C; 0.5 h; Inert atmosphere; 3: EtZnCl; 2-(4-iodophenoxy)-N,N-dimethylethanamine stereoselective reactionFurther stages;

1: (4-methoxymethoxy)phenylphenylacetylene With Me3SnLi in tetrahydrofuran; hexane T=0°C; 3 h; Inert atmosphere; 2: ethyl iodide in tetrahydrofuran; hexane T=0 - 20°C; 3 h; Inert atmosphere; 3: 2-(4-iodophenoxy)-N,N-dimethylethanamine stereoselective reactionFurther stages;

1: (4-methoxymethoxy)phenylphenylacetylene With Me3SnLi in tetrahydrofuran; hexane T=0°C; 3 h; Inert atmosphere; 2: With zinc(II) chloride in tetrahydrofuran; hexane T=0 - 20°C; 0.5 h; Inert atmosphere; 3: EtZnCl; 2-(4-iodophenoxy)-N,N-dimethylethanamine stereoselective reactionFurther stages;

1: (4-methoxymethoxy)phenylphenylacetylene With Me3SnLi in tetrahydrofuran; hexane T=0°C; 3 h; Inert atmosphere; 2: ethyl iodide in tetrahydrofuran; hexane T=0 - 20°C; 3 h; Inert atmosphere; 3: 2-(4-iodophenoxy)-N,N-dimethylethanamine stereoselective reactionFurther stages;

(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium hydroxide; 3,5-dimethoxy-phenol; [Pt(PPh3)4]; trifluoroacetic acid; 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl-4',4',5',5'-tetramethyl-1,3,2-dioxaborolane 1.) DMF, 80 deg C, 2.) DME, 25 deg C, 18 h, 3.) 25 deg C, 18 h, 4.) CH2Cl2; Yield given. Multistep reaction;

sodium hydroxide; tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0) in tetrahydrofuran; hexane T=60°C; 48 h;

sodium carbonate; tetrakis(triphenylphosphine) palladium(0) in ethylene glycol dimethyl ether; water Suzuki-Miyaura cross-coupling; 18 h; Heating;

1.1: 83 percent / CuI; Et3N / PdCl2(PPh3)2 / tetrahydrofuran / 22 °C 2.1: toluene; tetrahydrofuran / 12 h / Heating 2.2: 72 percent / Pd(PPh3)4 / toluene; tetrahydrofuran / 24 h / Heating 3.1: 96 percent / Dess-Martine periodinane / CH2Cl2 / 14 h / 22 °C 4.1: t-BuOK / tetrahydrofuran / 2 h / Heating 4.2: 81 percent / tetrahydrofuran / 12 h / 22 °C 5.1: 85 percent / H2 / Pd/C / ethyl acetate / 2 h / atmospheric pressure View Scheme

1-methyl-pyrrolidin-2-one; tris-(dibenzylideneacetone)dipalladium(0); copper(l) iodide; triphenyl-arsane; lithium chloride T=45°C; 48 h;

Pd0(tris(tert-butyl)phosphine)2; sodium hydroxide in tetrahydrofuran; water T=60°C; Suzuki-Miyaura Coupling; Overall yield = 80 percent; chemoselective reaction;