Synthesis, Characterization and Catalytic Application of Molecular and Gold Nanoparticle-Supported N-Heterocyclic Carbene Gold (I) Complexes

• Main Authors: Wang, Chien-Shun, 王建舜
• Other Authors: Yu, Shuchun Joyce
• Format: Others
• Language: zh-TW
• Published: 2015
• Online Access: http://ndltd.ncl.edu.tw/handle/77k3sn

碩士 === 國立中正大學 === 化學暨生物化學研究所 === 103 === We have successfully synthesized molecular and gold nanoparticle-supported N-heterocyclic carbene (NHC) gold(I) complexes which are [Mes-Au-Cl] (4) and RS-Au-SMes-AuCl (11). (Mesbim)HBr (2) has been treated with Ag2O to afford transfer agent. [Mes-Au-Cl] (4) has been synthesizd by transmetalation of the transfer agent in the presence of AuS(Me)2Cl (3). The complex (4) was characterizd by NMR, FT-IR, and ESI-Mass spectroscopies. At the same time, the octanethiolate protected gold nanoparticles (AuNPs), Au-SR (R = C8H17), were functionalized with (Mesbim)(CH2)11SH (8) to give mixed thiolate-covered AuNPs, RS-Au-SMes (10). Further reaction of the transfer agent which RS-Au-SMes (10) treated with Ag2O to afford with AuS(Me)2Cl (3) generated the desired hybrid catalyst RS-Au-SMes-AuCl (11) in quantitative yield. Since (11) is soluble (well-dispersed) in many organic solvents and can be precipitated and re-dissolved, the structure can be readily characterized by FT-IR, solution NMR, and TEM. The majority of reactions developed with Au complexes have exploited the propensity of Au to activate carbon-carbon π-bonds. Herein we demonstrated the free- and the AuNPs-supported gold complexes exhibited great catalytic activity towards hydroamination and hydration. In addition, the hybrid catalyst can be effectively recovered from reaction mixtures and can be recycled for twelve times without any significant loss of catalytic reactivity. Finally, we have demonstrated that these catalyses can be further accelerated under microwave irradiation condition. This approach seems to meet the urgent needs of sustainable development of chemistry. Key words : catalyst, N-heterocyclic carbene gold(I) complexes