Farmer Marcus E, Wang Peng, Shi Hang, Yu Jin-Quan
Department of Chemistry, The Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, California 92037.
ACS Catal. 2018 Aug 3;8(8):7362-7367. doi: 10.1021/acscatal.8b01599. Epub 2018 Jul 5.
Palladium catalyzed -C-H functionalization enabled by transient mediators has the potential to extend the utility of directed C-H functionalization to remote positions. However, there have been no reports of palladium catalyzed C-H functionalization of aromatic aldehyde derivatives, which are highly versatile intermediates in organic synthesis. Herein we report the development of a directing group that, in the presence of a norbornene derived mediator and an appropriate pyridone ligand, allows palladium catalyzed C-H functionalization of masked aromatic aldehydes. Mechanistic insight regarding the impact of the directing group length on this catalysis is also discussed.
由瞬态介质实现的钯催化的-C-H官能团化有潜力将定向C-H官能团化的应用扩展到远程位置。然而,尚未有关于钯催化芳族醛衍生物的C-H官能团化的报道,芳族醛衍生物是有机合成中用途广泛的中间体。在此,我们报道了一种导向基团的开发,在降冰片烯衍生的介质和合适的吡啶酮配体存在下,该导向基团可实现钯催化的掩蔽芳族醛的C-H官能团化。还讨论了关于导向基团长度对该催化影响的机理见解。