| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5276523 | Tetrahedron Letters | 2007 | 5 Pages |
Trifluoromethylated enynyl sulfones 3 were reacted with 2-4 equiv of phenyl, n-hexyl, trimethylsilyl, or triisopropylsilyl substituted ethynyllithium reagents in THF or ether at 0 °C to give trifluoromethylated enediynes 6 (Z)-stereoselectively in 41-96% yields. The reactions of β-fluoro-β-trifluoromethylvinyl sulfone 5 with same ethynyllithium reagents (4 equiv) afforded the corresponding enediynes 6 in 41-90% yields. The cross-coupling reactions of 6 bearing TMS group with aryl iodides in the presence of Pd(PPh3)2Cl2, Ag2CO3, and n-Bu4NBr provided the corresponding enediynes 6 in 20-71% yields. Dimerization of (Z)-6 bearing TMS group in the presence of CuBr2 and K2CO3 yielded dimer (Z,Z)-7 in good yield.
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