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- Representative procedure: to a solution of 3-hydroxy-1-iodopropyne (0.20 g, 1.1 mmol), phenylacetylene (145 L, 1.32 mmol), (pph3)2PdCl2 (21 mg, 0.03 mmol and Cul14 (6 mg, 0.03 mmol) in THF (8 ml) and under a nitrogen atmosphere was added diisopropylamine (0.3 ml, 2 mmol). After 1.5 hr at room temperature, the mixture was diluted with ether, extracted with dilute acid, water and brine, then dried (MgSO4). Purification using flash chromatography gave a 79% yield of 1-hydroxy-5-phenyl-2,4-pentadiyne
- Lee , G. C. M. , Tobias , B. , Holmes , J. M. , Harcourt , D. A. and Garst , M. E. 1990 . J. Am. Chem. Soc. , 112 : 9330 While this manuscript was in preparation, a synthesis of diynes using Pd-Cu cayalysis in triethylamine was reported in which it was observed that the copper (I) co-catalyst was essential for coupling