bis(η3-allyl-μ-chloropalladium(II)); P(C6H4)CH(C(CH3)C(Si(CH3)3))2 in tetrahydrofuran; acetonitrile T=20°C; Negishi coupling reaction; 2 h;

potassium phosphate; 1,1'-bis(diphenylphosphanyl)ferrocenenickel(II) chloride in toluene T=110°C; Suzuki-Miyaura Coupling; 24 h; Schlenk technique;

pyridine; tetra-n-butylammonium tetrafluoroborate in acetonitrile T=20°C; Electrolysisiron rod as anode; stainless steel grid as cathode;

water; triethylamine; Pd(OAc)2EnCatTM in N,N-dimethyl-formamide T=85°C; Suzuki-Miyaura reaction;

Ni(PCy3)2Cl2 in tetrahydrofuran; 1-methyl-pyrrolidin-2-one T=90°C; Negishi coupling reaction; 8 h; Inert atmosphere;

1.1: iPrMgCl / tetrahydrofuran; 1,2-dimethoxy-ethane / -20 °C 2.1: CuCN*2LiCl / 1,2-dimethoxy-ethane; tetrahydrofuran / 0.17 h / -20 °C 2.2: 72 percent / Fe(acac)3 / 1,2-dimethoxy-ethane; tetrahydrofuran / 3 h / -20 - 80 °C View Scheme

1: 4-iodobenzoic acid ethyl ester With isopropylmagnesium chloride in tetrahydrofuran; ethylene glycol dimethyl ether T=-20°C; 0.25 h; 2: With copper (I) cyanide in tetrahydrofuran; ethylene glycol dimethyl ether T=-20°C; 0.166667 h; 3: para-iodobenzonitrile With Fe(acac)3 in tetrahydrofuran; ethylene glycol dimethyl ether T=-20 - 80°C; 3 h; Product distribution / selectivity;

tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran T=25°C; Negishi cross-coupling; 2 h; Inert atmosphere;

1: potassium hydroxide / tetrahydrofuran / 20 °C 2: 1,1'-bis(diphenylphosphanyl)ferrocenenickel(II) chloride; potassium phosphate / toluene / 24 h / 110 °C / |Schlenk technique View Scheme