利用NS-MCM-41-Pd催化Borylation和 Suzuki反應以及One-pot的應用

Abstract

ABSTRACT Title：Borylation and Suzuki coupling catalyzed by NS-MCM-41-Pd and its One-pot application Pages：89 School：National Taipei University of Technology Department：Institute of Organic and Polymeric Materials Time：July, 2007 Degree：Master Researcher：Chun-Chin Chou Advisor:Fu-Yu Tsai Keywords：suzuki coupling, mesoporous material, palladium complex The use of transition metal as a catalyst plays an important role in organic synthesis in modern industry. Generally, homogeneous catalysts could get better yields under mild conditions, but difficult to be separated from the reaction mixtures after reaction finishing and the residue of the catalyst may destroy the purity and characteristics of the products. On the other hand, heterogeneous catalysts could be easily recovered by simple separation after reaction done and reuse for the next reaction. Herein, we utilized nanosized mesoporous silica materials, NS-MCM-41 (nano-sized MCM-41), as an inorganic solid support and grafting the bipyridyl palladium complex onto the wall to be a heterogeneous catalyst. The physical properties of this material is steady and the worm-hole like structure of the channels enables reactants, salts and products could easily through-out the channels without blockade. Since there is large surface area (around 588 m2/g) inside the channels and the surface has a plenty of silanol group, we can modify complex include catalyst onto NS-MCM-41 by physic adsorption or chemical bonding. This thesis reports that the employment of NS-MCM-41-Pd in the formation of arylboronates and then these products are used as reactants for Suzuki coupling for its one-pot application. The content is composed of two parts: in the first part, we use NS-MCM-41-Pd as a catalyst that is applied on the borylation of aryl halides and pinacolborane; and in the second part, NS-MCM-41-Pd system is employed for Suzuki coupling of aryl halides and arylboronates. Finally, we directly try to proceed one-pot borylation/Suzuki coupling (BSC) reaction. The detail of the activities, recycled properties and leach out studies of NS-MCM-41-Pd for these reactions are discussed in this thesis.