Please use this identifier to cite or link to this item: http://scholarbank.nus.edu.sg/handle/10635/107372
Title: HALOGEN CHEMISTRY: BROMINATION AND FLUORINATION VIA C-H FUNCTIONALIZATION AND THEORETICAL INVESTIGATION OF HALOGEN BONDING IN CATALYSIS
Authors: KEE CHOON WEE
Keywords: Bromination,Fluorination,DFT,Halogen,C-H functionalization,Photochemistry
Issue Date: 24-Jan-2014
Citation: KEE CHOON WEE (2014-01-24). HALOGEN CHEMISTRY: BROMINATION AND FLUORINATION VIA C-H FUNCTIONALIZATION AND THEORETICAL INVESTIGATION OF HALOGEN BONDING IN CATALYSIS. ScholarBank@NUS Repository.
Abstract: This thesis presents our works on the bromination and fluorination of sp3 C-H bond via photochemistry and our theoretical investigations on guanidine catalyzed asymmetric reactions and pentanidium catalyzed phase transfer synthesis of chiral sulfoxide. We have extended the synthetic application of visible light photoredox catalysis to bromination of sp3 C-H bond (aliphatic and benzylic) with inexpensive Eosin Y disodium salt as photoredox catalyst and CBr4 serve as Br source. We have also developed a photo-fluorination reaction catalyzed by an organo-photocatalyst. The reaction can be performed with common low power household lamps. The reaction is selective for electron rich sp3 C-H bonds due to the involvement of cationic N-radical in hydrogen abstraction. In the theoretical section, we investigated guanidine catalyzed enantioselective desymmetrization of meso-aziridne, decarboxylative Mannich reaction and enantiodivergent and ¿-Selective allylic amination. We have also study the use of halogen bond in pentanidium catalyzed phase transfer synthesis of sulfoxide.
URI: http://scholarbank.nus.edu.sg/handle/10635/107372
Appears in Collections:Ph.D Theses (Open)

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