Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.
J Am Chem Soc. 2012 Jul 18;134(28):11667-73. doi: 10.1021/ja303181m. Epub 2012 Jul 6.
The Suzuki-Miyaura reaction has become one of the more useful tools for synthetic organic chemists. Until recently, there did not exist a direct way to make the most important component in the coupling reaction, namely the boronic acid. Current methods to make boronic acids often employ harsh or wasteful reagents to prepare boronic acid derivatives and require additional steps to afford the desired boronic acid. The scope of the previously reported palladium-catalyzed, direct boronic acid synthesis is unveiled, which includes a wide array of synthetically useful aryl electrophiles. It makes use of the newly available second generation Buchwald XPhos preformed palladium catalyst and bis-boronic acid. For ease of isolation and to preserve the often sensitive C-B bond, all boronic acids were readily converted to their more stable trifluoroborate counterparts.
铃木-宫浦反应已成为合成有机化学家更有用的工具之一。直到最近，还没有直接的方法来制备偶联反应中最重要的组成部分，即硼酸。目前制备硼酸的方法通常使用苛刻或浪费的试剂来制备硼酸衍生物，并需要额外的步骤来获得所需的硼酸。揭示了先前报道的钯催化、直接硼酸合成的范围，其中包括广泛的合成有用的芳基亲电试剂。它利用了新的可用的第二代 Buchwald XPhos 预成型钯催化剂和双硼酸。为了便于分离并保持通常敏感的 C-B 键，所有硼酸都很容易转化为更稳定的三氟硼酸盐。
