Pd-Catalyzed Homologation of Arylboronic Acids as a Platform for the Diversity-Oriented Synthesis of Benzylic C-X Bonds
Pd-Catalyzed Homologation of Arylboronic Acids as a Platform for the Diversity-Oriented Synthesis of Benzylic C-X Bonds
复制标题
Pd 催化芳基硼酸同系化作为苯甲基 C-X 键多样性合成的平台
作者：
Watson A
我们报道了一个合成苄基C-X键的平台。苄基硼酸频哪醇（Bpin）酯是有用的合成中间体，但在商业上并不常见，导致制备通常依赖于化学计量的金属化。Pd催化的芳基硼酸的形式同系化提供了获得这些化合物的途径，这些化合物又允许从Pd和Cu介导的交叉偶联或氧化过程形成C-C、C-O和C-N键。这提供了多种苄醇、二芳基甲烷、苄胺和苄醚。公开了局限性，并且通过产生美克洛嗪的类似物进一步证明了实用性。
We report a synthetic platform for the formation of benzylic C–X bonds. Benzylboronic acid pinacol (Bpin) esters are useful synthetic intermediates but are commercially uncommon, leading to preparations that typically rely upon stoichiometric metalation. Pd-catalyzed formal homologation of arylboronic acids provides access to these compounds that, in turn, allow the formation of C–C, C–O, and C–N bonds from Pd- and Cu-mediated cross-coupling or oxidative processes. This affords a wide variety of benzylic alcohols, diarylmethanes, benzyl amines, and benzyl ethers. Limitations are disclosed, and the utility is further demonstrated by the generation of analogues of meclizine.