2,6-di-tert-butyl-4-methyl-phenol; lithium chloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride in N,N-dimethyl-formamide T=70°C; P=1520 Torr; 4 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 70°C under 1 atm CO for 4 h; cooled to room temp., dild. with ether, filtered, filtrate washed with water and satd. NaCl soln., dried, concd., chromd. (flash column, hexanes/EtOAc);

NiO2 in diethyl ether 0 deg C, 30 min --> r.t.;

1: 1) s-BuLi / 1) TMEDA/hexane, -78 deg C, 2 h -->0 deg C, 10 min; 2) TMDA/hexane, 0 deg, C, 2 min 2: 90 percent / nickel peroxide / diethyl ether / 0 deg C, 30 min --> r.t. View Scheme

1: 1) s-BuLi / 1) TMEDA/hexane, -78 deg C, 2 h -->0 deg C, 10 min; 2) TMDA/hexane, 0 deg, C, 2 min 2: 90 percent / nickel peroxide / diethyl ether / 0 deg C, 30 min --> r.t. View Scheme

1: 94 percent / methanol 2: 1) s-BuLi / 1) TMEDA/hexane, -78 deg C, 2 h -->0 deg C, 10 min; 2) TMDA/hexane, 0 deg, C, 2 min 3: 90 percent / nickel peroxide / diethyl ether / 0 deg C, 30 min --> r.t. View Scheme

iron(III) chloride in toluene T=20°C; 48 h;