1: 77 percent / PPTS / benzene / 3.5 h / Heating 2: dppf; N(Me)4Br / (Pd(π-allyl)Cl)2 / CH2Cl2; H2O / 2.5 h / 20 °C View Scheme

1,1'-bis-(diphenylphosphino)ferrocene; [14C]-Tetramethylammonium bromide; bis(η3-allyl-μ-chloropalladium(II)) in dichloromethane; water T=20°C; 2.5 h; Title compound not separated from byproducts;

1.1: O3; pyridine / CH2Cl2 / -78 °C 1.2: 66 percent / PPh3 / CH2Cl2 / 4 h / -78 - 20 °C 2.1: 77 percent / PPTS / benzene / 3.5 h / Heating 3.1: dppf; N(Me)4Br / (Pd(π-allyl)Cl)2 / CH2Cl2; H2O / 2.5 h / 20 °C View Scheme

in N,N-dimethyl-formamide T=0°C; 5 h;

toluene-4-sulfonic acid in toluene 4 h; Heating;

in N,N-dimethyl-formamide T=0°C; 0.333333 h;

1: HIO4*2H2O / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C 2: p-TsOH / toluene / 5 h / Heating 3: 65 percent / K2CO3 / methanol / 10 h 4: 97 percent / N-chlorosuccinimide-DMS / CH2Cl2 / 6 h / 0 °C 5: 86 percent / dimethylformamide / 5 h / 0 °C View Scheme