Palladium-Catalyzed N-Allylation ofNaphthylamines and C-Allylation of Cyclic 1,3-Diones in Water

• Main Authors: Yi-Jen Shue, 徐怡真
• Other Authors: Shyh-Chyun Yang
• Format: Others
• Language: zh-TW
• Published: 2012
• Online Access: http://ndltd.ncl.edu.tw/handle/23126535682615464544

博士 === 高雄醫學大學 === 藥學研究所 === 100 === Allylic substitution is a fundamental transformation in organic synthesis and also is one of the most powerful tools for the formation of carbon-carbon and carbon-heteroatom bonds. Transition metal-mediated C- and N-allylation reactions are very constructive for further investigating because of their broad substrate scope. The most of the studies have merely focused on Pd(II) complexes, which are the proven most active and multi-functional catalysts. The processes have been shown to proceed by attack of nucleophiles on intermediate ??3-allylpalladium(II) complexes generated by oxidative addition of allylic compounds to a Pd(0) complex. Since green chemistry processes and concerns over the environmental impacts of using volatile organic solvents, the promising potential of water and other non-conventional solvents has become highly noteworthy in designing organic syntheses. Furthermore, water has become as a highly recommended solvent for organic reactions in terms of cost, safety, availability, and environmental concerns. In this study, we divided into two parts to discuss the palladium catalyzed N- and C-allylation in water: (i) Simple palladium-catalyzed C-N bond formation for poor nucleophilicity of aminonaphthalenes. (ii) Activator-free and one-pot C-allylation by simple palladium catalyst in water. The reactions not only worked well, but also were air stable, economically viable and environmentally friendly