Department of Chemistry, University of California, and Division of Chemical Sciences, Lawrence Berkeley National Laboratory, Berkeley, California 94720, United States.
J Org Chem. 2010 Nov 19;75(22):7863-8. doi: 10.1021/jo101793r. Epub 2010 Oct 29.
The Rh(I)-catalyzed direct arylation of azines has been developed. Quinolines and 2-substituted pyridines couple with aryl bromides to efficiently afford ortho-arylated azine products using the commercially available and air-stable catalyst [RhCl(CO)2]2. Electron-deficient and electron-rich aromatic bromides couple in good yields, and hydroxyl, chloro, fluoro, trifluoromethyl, ether, and ketone functionalities are compatible with the reaction conditions. Aroyl chlorides also serve as effective azine coupling partners to give ortho-arylation products via a decarbonylation pathway.
已开发出 Rh(I)催化的嗪的直接芳基化反应。喹啉和 2-取代吡啶与芳基溴化物反应，使用市售且稳定的催化剂[RhCl(CO)2]2 有效地得到邻位芳基化嗪产物。缺电子和富电子的芳基溴化物以良好的收率偶联，并且羟基、氯、氟、三氟甲基、醚和酮官能团与反应条件兼容。芳酰氯也可以作为有效的嗪偶联试剂，通过脱羰途径得到邻位芳基化产物。
