Molander Gary A, Sandrock Deidre L
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA.
J Am Chem Soc. 2008 Nov 26;130(47):15792-3. doi: 10.1021/ja807076d.
A method was developed for the hydroboration of alkenyl-containing organotrifluoroborates to generate dibora intermediates. The reactivity differences between organotrifluoroborates and trialkylboranes facilitated the cross-coupling of the borane moiety of these intermediates in a highly chemoselective fashion with aryl halides, leaving the trifluoroborate intact for subsequent transformation. A one-pot hydroboration/two-directional cross-coupling sequence was also demonstrated, providing the fully elaborated products in good yields. These conditions were also amenable in the cross-coupling of trialkylboranes to halo-containing organotrifluoroborates. The stability of the trifluoroborate moiety to these conditions allows simple and efficient strategies for complex molecule construction.
开发了一种用于含烯基有机三氟硼酸盐硼氢化以生成二硼中间体的方法。有机三氟硼酸盐和三烷基硼烷之间的反应性差异促进了这些中间体的硼烷部分与芳基卤化物以高度化学选择性的方式进行交叉偶联，使三氟硼酸盐保持完整以便后续转化。还展示了一锅法硼氢化/双向交叉偶联序列，以良好的产率提供了完全精细的产物。这些条件也适用于三烷基硼烷与含卤有机三氟硼酸盐的交叉偶联。三氟硼酸盐部分对这些条件的稳定性允许采用简单有效的策略来构建复杂分子。
