1: 5-(3-hexylthiophen-2-yl)-3-hexylthiophene With 2,2,6,6-tetramethyl-piperidine; ethyl magnesium chloride in tetrahydrofuran T=20°C; 24 h; Schlenk techniqueInert atmosphereReflux; 2: 2-bromo-3-(n-hexyl)thiophene With [NiCl2(N,N'-bis[(2,6-diisopropylphenyl)imidazol]-2-ylidene)(PPh3)] in tetrahydrofuran T=60°C; 24 h; Schlenk techniqueInert atmosphere;

tetrakis(triphenylphosphine) palladium(0) in toluene T=90°C; Stille Cross Coupling; Inert atmosphereSchlenk techniqueLarge scale;

1: 5-(3-hexylthiophen-2-yl)-3-hexylthiophene With 2,2,6,6-tetramethyl-piperidine; ethyl magnesium chloride Inert atmosphere; 2: 2-chloro-3-(n-hexyl)-thiophene With [NiCl2(N,N'-bis[(2,6-diisopropylphenyl)imidazol]-2-ylidene)(PPh3)] T=60°C; 22 h; Inert atmosphere;

1.1: (2,2,6,6-tetramethylpiperidinyl)MgCl*LiCl / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere 1.2: 20 h / 60 °C / Inert atmosphere 2.1: 2,2,6,6-tetramethyl-piperidine; ethyl magnesium chloride / tetrahydrofuran / 24 h / 66 °C / Inert atmosphere 2.2: 26 h / 60 °C / Inert atmosphere View Scheme

1.1: (2,2,6,6-tetramethylpiperidinyl)MgCl*LiCl / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere 1.2: 20 h / 60 °C / Inert atmosphere 2.1: 2,2,6,6-tetramethyl-piperidine; ethyl magnesium chloride / tetrahydrofuran / 24 h / 66 °C / Inert atmosphere 2.2: 26 h / 60 °C / Inert atmosphere View Scheme

1.1: N-bromosuccinmide / acetic acid / 0.5 h 1.2: 0.17 h 2.1: Aliquatreg; 336; tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene / 20 h / |Reflux View Scheme

tetrakis(triphenylphosphine) palladium(0); Aliquatreg; 336; sodium carbonate in toluene Suzuki Coupling; 20 h; Reflux;