Synthesis and Applications of Phenanthrenes

• Main Authors: Yu-DeLin, 林育德
• Other Authors: Yao-Ting Wu
• Format: Others
• Language: zh-TW
• Published: 2012
• Online Access: http://ndltd.ncl.edu.tw/handle/72707064204303335213

碩士 === 國立成功大學 === 化學系碩博士班 === 100 === Phenanthrene derivatives are an important skeleton in many useful compounds, including alkaloids of phenanthroindolizidines, organic semiconductors and elementary subunit of buckminsterfullerene. For this reason, the goal in this research is to develop a simple synthetic method for the generation of phenanthrenes. The scope and limitations of the reactions were studied, numerous phenanthrenes were efficiently generated by Palladium-catalyzed cycloaddition of various 2,2'-diiodobiphenyls with alkyne in moderate yield to good yield. The optimized method was applied in the synthesis of phenanthroindolizidine alkaloids. Palladium-catalyzed cycloaddition of 2,2'-diiodobiphenyl with the (S)-2-(3-trimethylsilyl-2-propynyl)pyrrolidine gave a moderate yield of the desilylated overcrowded 4,5-disubstituted phenanthrene, which was then converted into phenanthroindolizidine by the Pictet-Spengler cyclization.