sodium hexamethyldisilazane in diethyl ether 3 h; Inert atmosphere;

1: 90 percent / propan-1-ol; H2O / 1 h / 70 °C 2: 85 percent / sodium borohydride / tetrahydrofuran 3: 59 percent / formic acid / 45 h / Heating 4: 42 percent / KH; dibenzo-18-crown-6 / tetrahydrofuran; various solvent(s) / 5 h / 23 °C View Scheme

1: 85 percent / sodium borohydride / tetrahydrofuran 2: 59 percent / formic acid / 45 h / Heating 3: 42 percent / KH; dibenzo-18-crown-6 / tetrahydrofuran; various solvent(s) / 5 h / 23 °C View Scheme

dibenzo-18-crown-6; potassium hydride 120 h; Inert atmosphere;

1: N-ethyl-N,N-diisopropylamine / Inert atmosphere 2: dibenzo-18-crown-6; potassium hydride / 120 h / Inert atmosphere View Scheme

in diethyl ether Et2O was added via cannula to mixt. of ligand and Pd compd. at -78°C; mixt. was stirred at -78°C for 30 min; warmed with stirring to room temp. over 2 h; ether removed (vac.); triturated with hexane; filtered in air; washed (hexane); elem. anal.;