Photocatalytic C-N addition amination of olefin

Department of Fine Chemicals, Dalian University of Technology, Dalian, China

^* Corresponding author: xinrui@dlut.edu.cn

Abstract

Amines widely exist in nature, wherein some of cyclic amines have crucially biological and physiological activities. They are also the basic blocks for the syntheses of important intermediates, raw materials or fine chemicals such as pharmaceuticals, pesticides and dyes. Amine synthesis by photocatalytic amination of phthalimide and olefins using porphyrin iron (III) or phthalocyanine iron(II) as photosensitizer was investigated in this paper. The results showed that the reactions selectively developed C-N addition and generated a series of compounds containing benzazepine structure with the highest yield of 99.0% at 30 °C. The scope of substrates was further examined and the results demonstrated that the reaction was effective to various olefins, especially to aliphatic olefins. In addition, the influence of the light source was further investigated. The simple, low-power, insect trap lamp (6 W, 365 nm) was used as the light source for the reaction, and a high yield of 95.0% was obtained. Therefore, the inspiring results provide a green and efficient method for the synthesis of compounds containing benzazepine structure.