diisobutylaluminium hydride in hexane; dichloromethane -78 deg C, 30 min then 23 deg C, 30 min;

sodium tetrahydroborate in methanol T=20°C;

1: dichloromethane / 3 h / 20 °C 2: sodium tetrahydroborate / methanol / 20 °C View Scheme

2,6-di-tert-butyl-4-methyl-phenol; 4 A molecular sieve; lithium chloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride in N,N-dimethyl-formamide T=90°C; P=760 Torr; 13 h;

LiCl; CO; dichloro{1,1'-bis(diphenylphosphino)ferrocene}palladium(II) in N,N-dimethyl-formamide the triflate and the stannane in DMF contg. the Pd catalyst and LiCl heated at 90°C under 1 atm CO for 13 h; cooled to room temp., dild. with ether, filtered, filtrate washed with water and satd. NaCl soln., dried, concd., chromd. (flash column, hexanes/EtOAc);

tributyl-amine; lithium chloride; tetrakis(triphenylphosphine) palladium(0) in acetonitrile P=760 Torr; Heating;

carbon tetrabromide; triphenylphosphine in acetonitrile 15 h; Heating;