1: p-methoxy-phenylmagnesium chloride With N,N,N',N,-tetramethylethylenediamine; zinc(II) chloride in tetrahydrofuran T=80°C; 0.25 h; microwave irradiation; 2: 4-bromo-benzaldehyde With bis-triphenylphosphine-palladium(II) chloride in tetrahydrofuran T=20°C; Negishi cross-coupling; 0.0833333 h;

in tetrahydrofuran T=1°C; 0.0833333 h;

1: in tetrahydrofuran T=-20°C; 2 h; 2: With sodium tetrahydroborate; iron(II) chloride in tetrahydrofuran T=-20 - 20°C; 2 h;

triphenylphosphine; Ni(II)/C in tetrahydrofuran Kumada coupling; 1 h; Heating;

in diethyl ether 0°C;

1: 80 percent / tetrahydrofuran / 1 h / -78 °C 2: 100 percent / KOH / ethanol / 20 °C 3: 85 percent / Co(III) o-phenylene-bis(N'-methyloxamidate) complex; O2; pivalaldehyde / CH2Cl2 View Scheme

1: p-methoxy-phenylmagnesium chloride With zinc dibromide in tetrahydrofuran; ethylpyrrolidin-2-one; 1- Inert atmosphereSchlenk tubeCooling; 2: 4-bromo-benzoic acid ethyl ester With 4-(N,N-dimethlyamino)pyridine; phosphonic acid diethyl ester; nickel dichloride in tetrahydrofuran; ethylpyrrolidin-2-one; 1- T=20°C; 48 h; Schlenk tubeInert atmosphere; 3: With ammonium chloride in tetrahydrofuran; ethylpyrrolidin-2-one; 1- Product distribution / selectivity;

1-methyl-pyrrolidin-2-one; cobalt(II) 2,4-pentanedionate in tetrahydrofuran T=15 - 20°C; 0.25 h;

1: With methanol in tetrahydrofuran T=-78 - 20°C; Inert atmosphere; 2: With trifluoroacetic anhydride in tetrahydrofuran T=20°C; 0.333333 h; regioselective reaction;

copper(l) iodide; manganese (II) chloride in tetrahydrofuran T=0 - 20°C; Inert atmosphere; stereospecific reaction;