EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST, UK.
Org Biomol Chem. 2019 May 28;17(20):5055-5059. doi: 10.1039/c9ob00561g. Epub 2019 May 3.
The Suzuki-Miyaura reaction is a cornerstone method for sp-sp cross-coupling in industry. There has been a concerted effort to enable the use of Ni catalysis as an alternative to Pd in order to mitigate cost and improve sustainability. Despite significant advances, ligand development for Ni-catalyzed Suzuki-Miyaura cross-coupling remains underdeveloped when compared to Pd and, as a consequence, ligands for Ni-catalyzed processes are typically taken from the Pd arena. In this study we evaluate the effect of using a similar Ni and Pd precatalyst based on a common bidentate ligand (dppf) in a head-to-head format for the most common type of biaryl couplings, establishing the practical implications of direct replacement of Pd with Ni, and identifying the potential origins of these observations in a mechanistic context.
铃木-宫浦反应是工业中 sp-sp 交叉偶联的基石方法。人们一直在努力使镍催化成为钯的替代物，以降低成本并提高可持续性。尽管取得了重大进展，但与 Pd 相比，Ni 催化的铃木-宫浦交叉偶联的配体开发仍不发达，因此，Ni 催化过程的配体通常取自 Pd 领域。在这项研究中，我们以最常见的联芳基偶联物为例，以头对头的形式评估了使用类似的 Ni 和 Pd 前催化剂（基于常见的双齿配体 dppf）的效果，确定了用 Ni 直接替代 Pd 的实际意义，并在机理背景下确定了这些观察结果的潜在来源。
