Studies On The Palladium-catalyzed Alkenylation Of Aromatic Amine Assisted By Directing Group

Palladium-catalyzed C-H activation reaction has become a hotspot in the research of the organic chemistry in recent years. It has emerged as one of the most efficient and straightforward for the constraction of drug molecules and organic natural molecules, which have received considerable attention and intensive study. This kind of reaction effectively increase the C-H functional activity and selectivity in the region through heteroatoms’ good coordination ability with palladium. Based on this, looking for new kinds of directing group which is easy to remove, easy to transform is the difficulty of C-H activation. In this thesis, we mainly studies the Pd(OAc)2 as the catalysis to achieve the C-H alkenyl reaction under a new directing group. The whole work is mainly composed of following three parts:In part one, the recent progresses on the studies of palladium-catalyzed alkenylation of aromatic amine assisted by directing group home and abroad, the significance and bases of the selection of the subject, the original points and the research techniques have been reviewed.In part two, a noval protocol for palladium-catalyzed ortho C–H alkenylation of oxalyl amide protected phenylpropylamine derivatives is described. The range of olefins were the broadest yet reported for this kind of C–H alkenylation reactions. The reaction reflects the powerful guidance capability and highly active of the oxalyl amide directing groups.In part three, a study on the palladium-catalyzed ortho C–H alkenylation of oxalyl amide protected β-arylethamines derivatives. It has the highly selective ortho-alkenylation of β-arylethamines under assistance of oxalyl amide, and the wide range of olefins is the broadest yet reported for this kind of C–H transformation.The structures of the products were identified by NMR and HRMS. And a possible reaction mechanism of the reaction has also been proposed.