Synthesis and Properties of N-Heterocyclic Carbene Metal Complexes and Their Application Toward Arylation of Heterocycle C-H Bonds

• Main Authors: Hsuan-jui Huang, 黃璿瑞
• Other Authors: Tiow-gan Ong
• Format: Others
• Language: zh-TW
• Published: 2013
• Online Access: http://ndltd.ncl.edu.tw/handle/86161346402594023647

碩士 === 國立臺灣科技大學 === 化學工程系 === 101 === Since the discovery of a stable N-heterocyclic carbene (NHC), there has been a spectacular explosive interest in employing NHC platforms as ancillary ligands for various metal complexes. The interest is stemmed from a desire of not only to understand the fundamentals behaviors of the metal-carbene bonding, but the emerging applications in small homogeneous catalysis. In our research effort, we have prepared a series of novel imidazolium salts precursors for amino-linked N-heterocyclic carbene ligands. These amino-linked imidazolium salts successfully reacted with Ag2O to afford air-stable silver carbene complexes 3. Silver carbene complexes 3 could then act as a carbene transfer agent for the synthesis of copper carbene complexes 4 or gold carbene complexes 5. These metal complexes have been characterized by multinuclear (1H, 13C) NMR spectroscopy, MS measurements and identity of those complexes are confirmed by single-crystal X-ray diffraction. In addition, we investigate the copper carbene complexes catalyzed arylation reaction and proved these copper carbene complexes shows promising activity, and the results have validated the importance of the cooperating effect invoked by t-Butyl moiety to assist the efficiency of this catalysis. Arylation reaction of caffeine can be catalyzed to afford variety of natural products and pharmaceuticals on the high yield.