A Study on the Silver-Mediated Multi-Substitution C-H Functionalization of 1,4-Benzoquinones

• Main Authors: Ching-Hua Pai, 白璟樺
• Other Authors: 洪豐裕
• Format: Others
• Language: zh-TW
• Published: 2017
• Online Access: http://ndltd.ncl.edu.tw/handle/06268041939642335588

碩士 === 國立中興大學 === 化學系所 === 105 === In this work, we report a silver-mediated C-H functionalization of benzoquinone (BQ) through stepwise and regioselective phosphination and amination reactions. Diphenylphosphine oxide and N-benzylideneaniline were employed as the reagents for constructing C-P and C-N bonds, respectively. Optimized reaction conditions for the formation of di-, tri-, or tetrasubstituted BQ as main product were found. The reaction conditions were found to be mild and the yields of di-substituted BQ are moderate to high. The reaction pathway might proceed through the formation of 2-phosphoryl hydroquinone intermediate via 1,4-addition of secondary phosphine oxides to BQ. Palladium complex was synthesized with di-substituted BQ as ligand. We also demonstrated that a di-substituted BQ can act as a bidentate ligand.