| Summary: | 碩士 === 國立中興大學 === 化學系所 === 99 === Abstract
The acetylenic compounds are important building block in the fields of pharmaceutical chemistry and organic synthesis. The transition metal catalyzed coupling reaction of terminal alkynes with aryl halides has become one of the most important methods for preparing functionalized alkynes. Palladium and copper co-catalyzed system is well known as Sonogashira reaction, however, palladium is not only expensive but also highly toxic. Thus, develop the system by using copper as the sole metal source has gain much attention in recent years. The first part of this thesis, we report a highly efficient catalytic system employs the combination of Cu2O (1 mol %) with bisphosphine ligand, giving the products in good to excellent yields.
Recently, aryl vinyl sulfides have been reported as drug candidates against drugresistant strains of tuberculosis and anthrax, in addition to many other drug-resistant Gram-positive bacteria. Addition of thiols to alkynes through a radical pathway is a common way to prepare these compounds, however, this method will produce the undesired regioisomers at the same time. Transition metals including palladium, cobalt and copper have been reported for coupling reaction of thiols with vinyl halides. The second part of this thesis, we report the first iron-catalyzed coupling reaction of thiols with vinyl halides in the presence of a bisphosphine ligand, giving the aryl vinyl sulfide in good yields.
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