Pd(CH2SiMe3)2(cod); t-Bu Brett Phos; cesium fluoride in toluene T=130°C; 12 h;

pyridine; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate T=150°C; 0.333333 h; microwave irradiation;

1: 71 percent / Pd(OAc)2; BINAP; Cs2CO3 / toluene / 80 °C 2: 100 percent / KOH / tetrahydrofuran / Heating 3: H2 / Pd/C View Scheme

sodium carbonate; tetrakis(triphenylphosphine) palladium(0) in ethylene glycol dimethyl ether Heating;

1: 3-methoxy-1-trifluoromethanesulfonyloxybenzene With 1,1'-bis-(diphenylphosphino)ferrocene; bis(1,5-cyclooctadiene)nickel (0); N,N-dicyclohexylmethylamine Heck Reaction; Inert atmosphereGloveboxSealed tube; 2: 4-methoxy-1-vinyl-benzene With (SPY-5-31)-dichloro-(κ2(C,O)-(2-isopropyloxybenzylidene))(1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene)ruthenium T=100°C; 20 h; GloveboxInert atmosphereSealed tube;

1: Et3N / 1,3-bis(diphenylphosphino)propane / Pd(OAc)2 / dimethylformamide / 2 h / 80 °C 2: 5percent HCl / 0.5 h View Scheme

1: diisopropylamine With n-butyllithium in tetrahydrofuran T=-78 - 20°C; 1 h; 2: 3-methoxy-1-trifluoromethanesulfonyloxybenzene in tetrahydrofuran T=-78 - 20°C; 0.166667 h; Further stages. Title compound not separated from byproducts.;

palladium diacetate; caesium carbonate; 2-(dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1’-biphenyl in toluene T=100°C; 1.5 h;

1.54H2O*Cl2Ni; ICy*HBF4 in tetrahydrofuran T=-10°C; Kumada coupling reaction; 1.5 h; Inert atmosphere;

in 1-methyl-pyrrolidin-2-one T=198 - 206°C; 2 h; microwave irradiation;