9 triyne 9 to a dmf 5 ml solution of 1 trimethylsilyl 1 3 pentadiyne 0 4 g 2 94 mmol under argon was added tbaf 0 8 g 3 mmol and several drops of water the dark brown solution was stirred for 2 h at room temperature then diluted with benzene 3 ml the benzene layer was washed with saturated brine 5 u00d7 5 ml after drying mgso 4 and filtering the solution was transferred to a flask containing 8 500 mg 0 96 mmol ph 3 p 2 pdcl 2 34 mg 0 048 mmol cui 9 mg 0 048 mmol and et 2 nh 1 ml the mixture was stirred under argon at room temperature for 40 h and then concentrated in vacuo ether 100 ml and water 25 ml were added the layers were separated the ether layer was washed with brine 3 u00d7 20 ml dried mgso 4 concentrated in vacuo and the residue purified by flash column chromatography 1 6 ch 2 cl 2 hexanes giving 9 as a yellow oil 0 25 g 57 yield 1 h nmr u03b4 7 15 7 3 m 10 h 6 99 d j 11 7 hz 1 h 6 90 d j 11 7 hz 1 h 4 09 s 2 h 4 06 s 2 h 1 98 s 3 h 0 20 s 9 h 13 c nmr u03b4 120 138 several 102 32 102 09 84 37 80 86.