Department of Chemistry, Faculty of Science and Technology, Keio University , 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan.
JST, ACT-C, 4-1-8 Honcho, Kawaguchi, Saitama, 332-0012, Japan.
Org Lett. 2017 Feb 17;19(4):794-797. doi: 10.1021/acs.orglett.6b03761. Epub 2017 Feb 6.
We report here the ruthenium-catalyzed selective monoarylation of aromatic ketones bearing two ortho carbon-heteroatom (O or N) bonds. Under the newly developed catalyst system consisting of RuHCl(CO)(PPr), CsF, and styrene, the C-O arylation of 2',6'-dimethoxyacetophenone with a phenylboronate gave the C-O monoarylation product selectively. The selective C-O monoarylation was applicable to a variety of arylboronates and aromatic ketones and proceeds with high regio- and chemoselectivities. A formal synthesis of altertenuol was also achieved using the C-O monoarylation of an aromatic ester as a key step.
我们在此报告了钌催化的含两个邻位碳杂原子（O 或 N）键的芳基酮的选择性单芳基化反应。在由 RuHCl(CO)(PPr)、CsF 和苯乙烯组成的新开发的催化剂体系下，2'，6'-二甲氧基苯乙酮与苯基硼酸酯的 C-O 芳基化反应选择性地得到了 C-O 单芳基化产物。选择性 C-O 单芳基化反应适用于多种芳基硼酸酯和芳香酮，并具有高区域和化学选择性。使用芳香酯的 C-O 单芳基化作为关键步骤，也实现了 altertenuol 的形式合成。
