Part I Transition metal-catalyzed trifluoromethylation of olefins Part II Biocompatible disulfide bridging reaction

• Main Author: Wu, Liuhai
• Other Authors: Loh Teck Peng
• Format: Theses and Dissertations
• Language: English
• Published: 2018
• Subjects: DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis; DRNTU::Science::Chemistry::Organic chemistry::Oxidation
• Online Access: https://hdl.handle.net/10356/88615; http://hdl.handle.net/10220/47074
• Institution: Nanyang Technological University

This thesis contains two parts. Part Ⅰ describes trifluomethylation of olefins and Part Ⅱ describes biocompatible disulfide bridging reactions. Copper-catalyzed trifluoromethylation of olefins with Langlois reagent was described. Excellent selectivity was achieved with styrene derivatives and mechanistic studies revealed the radical process is involved (chapter 2). Visible light-induced trifluoromethylation of fluorinated alkenes via C(sp2&sp3)–F bond functionalization using Langlois reagent as CF3 source was discussed. The reactions proceeded efficiently via trifluoromethyl radical addition followed by β-fluorine elimination process, providing a new entry to multifluorinated alkenes in moderate to good yields with excellent stereoselectivity (chapter 3). In chapter 4, a new class of biocompatible site-specific reagents, undergoing disulfide bridging with thiol substrates efficiently in buffer solution, was described. Disulfide rebridging of N-Ac-oxytocin with the reagent was successfully achieved in high yield.