Date on Master's Thesis/Doctoral Dissertation
12-2011
Document Type
Doctoral Dissertation
Degree Name
Ph. D.
Department
Chemistry
Committee Chair
Hammond, Gerald B.
Author's Keywords
Gold catalysis; Gold catalyzed hydration; Fluorine chemistry; Flurohydrin; Functionalized hydration; Metal-fluorine intermediate
Subject
Fluorine compounds--Synthesis; Catalysts
Abstract
Our research activities are based on the catalytic systems that provide resource-saving synthetic methodologies through gold-catalyzed reactions of alkynes and alkenes. We have worked on three applications: i) an effective and straightforward hydration of 3-alkynoates catalyzed by gold (III); this mild and atom-economical method can be used effectively with a wide range of substrates with high regioselectivity; ii) an efficient monofluorination of allyl silanes using Selectfluor has been achieved without gold catalysts; iii) a fluorine-enabled cationic metal species, generated by fluorination of a low valence gold(l) complex, catalyzed the hydration of alkynes to give a-substituted-a-fluoroketones in one pot under mild conditions. The latter allowed a diverse range of fluorine building blocks or targets to be made available using tools that are amenable in combinatorial or parallel synthesis conditions in drug discovery laboratories or process chemistry.
Recommended Citation
Wang, Weibo, "Gold catalysis and its applications in synthesis of fluorinated organic compounds." (2011). Electronic Theses and Dissertations. Paper 1518.
https://doi.org/10.18297/etd/1518
