Synthesis of Aryl Ethers: Metal-Free Arylation of Alcohols using Diaryliodonium Salts
2015 (English)Licentiate thesis, comprehensive summary (Other academic)
This thesis contains two parts showing different metal-free methods to synthesize aryl ethers using hypervalent iodine reagents, more specifically diaryliodonium salts. The first part describes arylation of benzylic and allylic alcohols and phenols in water using the easily accessible base sodium hydroxide. Chemoselectivity of phenols in aqueous media is discussed and limitations of the reaction are presented.
The second part describes an arylation of aliphatic alcohols at room temperature with short reaction time and no excess of reagents are required. The scope of the methodology was investigated and showed that electron-deficient iodonium salts worked efficiently, but unfortunately electron-rich was not compatible with the reaction conditions. The methodology was applied in a formal synthesis of Butoxycaine.
Place, publisher, year, edition, pages
Stockholm: Department of Organic Chemistry, Stockholm University , 2015. , 42 p.
IdentifiersURN: urn:nbn:se:su:diva-116183OAI: oai:DiVA.org:su-116183DiVA: diva2:802623
2015-04-30, Magnélisalen, 10:00 (English)