Milton Edward J, Fuentes José A, Clarke Matthew L
School of Chemistry, University of St Andrews, EaStCHEM, St Andrews, Fife, UK.
Org Biomol Chem. 2009 Jun 21;7(12):2645-8. doi: 10.1039/b907784g. Epub 2009 May 15.
Changing the activator from tetrabutyl ammonium fluoride (TBAF) to sodium hydroxide unexpectedly switches the catalytic pathway of the Hiyama coupling reaction of vinyl trialkoxysilanes with aryl bromides into a Pd catalysed C-O bond forming reaction; if the correct conditions are used, high yields of aryl-alkyl ethers are observed. In addition, coupling between readily available tetraalkoxysilanes and aryl bromides can also be realised with NaOH or TBAF activation. The reactions take place in only 20 minutes if microwave heating is employed.
将活化剂从四丁基氟化铵（TBAF）换成氢氧化钠，意外地将乙烯基三烷氧基硅烷与芳基溴化物的硅氢加成反应的催化途径转变为钯催化的碳-氧键形成反应；如果使用正确的条件，可以观察到芳基-烷基醚的高产率。此外，通过氢氧化钠或四丁基氟化铵活化，也可以实现现成的四烷氧基硅烷与芳基溴化物之间的偶联。如果采用微波加热，反应仅需20分钟即可完成。
