n-butyllithium in tetrahydrofuran (N2); to a soln. of BuLi the acetylene was added at -78°C, soln. was allowed to warm to 0°C over 0.5 h, metal chloride was slowly added, after stirring at -78°C for 0.5 h, the mixt. was warmed up to room temp. and stirred; the mixt. was quenched with water and extd. 3 times with ether, the combined organic phases were dried over MgSO4 and filtered, solvent was removed under reduced pressure, distillation;

in tetrahydrofuran

zinc dibromide in tetrahydrofuran Bu3SnOMe (1 mmol) and Me3SiCCH (2 mmol) stirred at room temp. for 3 h inpresence of ZnBr2 catalyst (0.05 mmol), quenched by H2O; extracted with Et2O, organic layer sepd., dried (MgSO4), volatiles evapd., residue deluted with AcOEt, washed with NH4F, ppt. filtered off, filtrate dried (MgSO4), volatiles evapd.; detd. by (1)H NMR;

T=100°C; 14 h; Sealed tube;

diphenylphosphine-based palladium(0) complex on MCM-41 in water; N,N-dimethyl-formamide T=60°C; Stille coupling; 6 h;

sodium in benzene byproducts: NaCCSi(CH3)3; the soln. of stannane was added to a suspn. of Na, the mixt. was stirred (18 h, 80°C), filtered under N2; the product was sepd. from filtrate by distn.;

diphenylphosphine-based palladium(0) complex on MCM-41 in water; N,N-dimethyl-formamide T=60°C; Stille coupling; 6 h;

tetrakis(triphenylphosphine) palladium(0) in toluene T=122°C; 36 h;

1: iodobenzene With diphenylphosphinoethane functionalized polystyrene resin-supported Pd(0) complex in N,N-dimethyl-formamide T=20°C; Stille Cross Coupling; 0.25 h; 2: trimethyl[(tributylstannyl)ethynyl]-silane in N,N-dimethyl-formamide T=65°C; Stille Cross Coupling; 9 h;

bis-triphenylphosphine-palladium(II) chloride in 1,2-dichloro-ethane T=84°C; 2 h;