The study of halogen bonding induced reaction

• Main Author: He, Wei
• Other Authors: Tan Choon Hong
• Format: Thesis-Doctor of Philosophy
• Language: English
• Published: Nanyang Technological University 2017
• Subjects: DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis
• Online Access: http://hdl.handle.net/10356/70992
• Institution: Nanyang Technological University

As a classic non-covalent bond interaction, halogen bonding is well studied in material sciences and crystal engineering, and its application in catalysis has attracted research attention in these years. A brief introduction of the properties of halogen bonding is described in the first chapter of this thesis. Due to the high directionality and high energy characteristics, halogen bonding has been widely used in crystal engineering, material science and even in the biological system. Based on these unique properties, an introduction to the background of halogen bond and recent development in catalysis is presented, which forms the basis for our proposed research design. We synthesized a series of novel halogen bond donors, and the structure and evidence of the presence of halogen bonding was proved by X-ray, ITC and NMR studies. The results of these halogen bond donors is presented in Chapter 2. In the next two chapters, these novel halogen bond donors were used as catalysts in the hydrogen transfer reduction of C=N bond compounds with Hantzsch ester and the [3+2] cycloaddition. In these two reactions, the C=N and the carbonyl compound were activated by halogen bond donor through halogen bonding, and product was obtained in good yield. The interaction between the substrate with halogen bond donor was confirmed by using NMR study and ITC.