Hanamoto Takeshi, Kobayashi Tomoko
Department of Chemistry and Applied Chemistry, Saga University, Honjyo-machi 1, Saga 840-8502, Japan.
J Org Chem. 2003 Aug 8;68(16):6354-9. doi: 10.1021/jo030111r.
The cesium fluoride (CsF)-assisted cross-coupling reaction of (1-fluorovinyl)methyldiphenylsilane (1) with aryl halides and aryl triflates was examined. The reaction with aryl iodides smoothly proceeded to afford the corresponding (1-fluorovinyl)arenes in the presence of a catalytic amount of CuI and Pd(PPh(3))(4) in aprotic polar solvents such as DMF, DMI, DMA, and NMP in good yields. A variety of functional groups (nitro, ester, ketone, and ether) on the aromatic rings can be tolerated under these mild conditions. Aryl iodides are superior to aryl bromides as the coupling reaction partner. The cross-coupling reaction of 1 with aryl triflates instead of aryl halides was also accomplished in the presence of tetrabutylammonium iodide (n-Bu(4)NI) as the additive under similar conditions.
研究了氟化铯（CsF）辅助下（1-氟乙烯基）甲基二苯基硅烷（1）与芳基卤化物和芳基三氟甲磺酸酯的交叉偶联反应。在非质子极性溶剂（如DMF、DMI、DMA和NMP）中，在催化量的CuI和Pd(PPh(3))(4)存在下，与芳基碘的反应顺利进行，以良好的产率得到相应的（1-氟乙烯基）芳烃。在这些温和条件下，芳环上的各种官能团（硝基、酯基、酮基和醚基）均可耐受。作为偶联反应伙伴，芳基碘优于芳基溴。在类似条件下，以碘化四丁铵（n-Bu(4)NI）为添加剂，1与芳基三氟甲磺酸酯而非芳基卤化物的交叉偶联反应也得以实现。
