Transition-Metal-Catalyzed Cross-Coupling Reaction of Aldehydes with Thiols

• Main Authors: Yu-Ting Huang, 黃鈺婷
• Other Authors: Chin-Fa Lee
• Format: Others
• Language: zh-TW
• Published: 2014
• Online Access: http://ndltd.ncl.edu.tw/handle/49385657711616642390

碩士 === 國立中興大學 === 化學系所 === 102 === In the first part of this thesis, the preparation of thioesters through the copper-catalyzed cross-coupling reaction of aldehydes with aryl thiols in the presence of tert-butyl hydroperoxide (TBHP) as an oxidant is described. Functional groups including chloro, bromo, iodo, nitrile, acetyl and thiophene are all tolerated by the reaction conditions employed. To our delight, the reactions were carried out in water without any surfactant. The second part of this thesis, we report the iron-catalyzed formation of thioesters from thiols and aldehydes. The reactions were carried out by using TBHP as an oxidant, and water or acetonitrile as solvent. Functional groups including chloro, bromo, trifluoromethyl, nitrile and heteroaryls including thiophene, furan and pyridine are all tolerated under the reaction conditions. The third part of this thesis is to develop an efficient approach for the preparation of thioesters through DTBP promoted thiols and aldehydes under metal-free and solvent-free conditions. This system not only shows good functional group tolerance, but also tolerates steric hinder substrates as coupling partners.