copper(l) iodide; triphenylphosphine; potassium carbonate in N,N-dimethyl-formamide T=160°C; 24 h;

sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) in benzene T=85°C; 22 h;

potassium hydroxide; copper(l) iodide; [(P{(C6H11)3})2Pd(Cl)2] in toluene T=80°C;

copper(l) iodide; potassium carbonate; triphenylphosphine in N,N-dimethyl-formamide T=160°C;

triethylamine; copper(l) iodide; triphenylphosphine; bis(dibenzylideneacetone)-palladium(0) Yield given;

(Me3CO)3Wlt;*gt;CCMe3 in toluene T=80°C; 8 h;

1.1: bis(triphenylphosphine)palladium(II)chloride; copper(I) iodide; triethylamine / 25 - 50 °C 2.1: iodomethane / 120 °C 3.1: 88 percent / copper(I) iodide; triethylamine; PdCl2(PPh3)2 4.1: iodomethane / 120 °C 5.1: copper(I) iodide; triethylamine; PdCl2(PPh3)2 6.1: iodomethane / 120 °C 7.1: potassium carbonate / methanol; diethyl ether 8.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 °C 8.2: copper(I) iodide; bis(dibenzylideneacetone)palladium(0); triphenylphosphine / triethylamine View Scheme

1.1: iodomethane / 120 °C 2.1: 88 percent / copper(I) iodide; triethylamine; PdCl2(PPh3)2 3.1: iodomethane / 120 °C 4.1: copper(I) iodide; triethylamine; PdCl2(PPh3)2 5.1: iodomethane / 120 °C 6.1: potassium carbonate / methanol; diethyl ether 7.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 °C 7.2: copper(I) iodide; bis(dibenzylideneacetone)palladium(0); triphenylphosphine / triethylamine View Scheme

piperidine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide in N,N-dimethyl-formamide T=60°C; 48 h;

1.1: 88 percent / copper(I) iodide; triethylamine; PdCl2(PPh3)2 2.1: iodomethane / 120 °C 3.1: copper(I) iodide; triethylamine; PdCl2(PPh3)2 4.1: iodomethane / 120 °C 5.1: potassium carbonate / methanol; diethyl ether 6.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 °C 6.2: copper(I) iodide; bis(dibenzylideneacetone)palladium(0); triphenylphosphine / triethylamine View Scheme