Department of Small Molecule Process Chemistry, Genentech, Inc. , South San Francisco, California 94080, United States.
Org Lett. 2017 Jun 2;19(11):3021-3024. doi: 10.1021/acs.orglett.7b01304. Epub 2017 May 22.
We describe the highly selective copper-catalyzed Ullmann-type coupling of bromoiodoarenes with oxazolidinones. 3,4,7,8-Tetramethyl-1,10-phenanthroline (MePhen) was identified as an optimal ligand promoting the desired C-N bond formation, while minimizing the competitive bromo-iodo exchange pathway that leads to formation of iodo-substituted and bis-coupled side products. The developed method is highly selective with a >98:2 ratio of the bromo- vs iodo-substituted compounds obtained in the isolated products.
我们描述了一种高选择性的铜催化的溴碘芳基与恶唑烷酮的Ullmann 型偶联反应。3,4,7,8-四甲基-1,10-菲咯啉（MePhen）被确定为一种最佳配体，促进所需的 C-N 键形成，同时最大限度地减少导致形成碘取代和双偶联副产物的竞争溴碘交换途径。所开发的方法具有高度选择性，在分离产物中获得的溴代与碘代化合物的比例大于 98:2。
