Efficient and High-Yielding Routes to Diaryliodonium Salts
Stockholm University, Faculty of Science, Department of Organic Chemistry2008 (English)Licentiate thesis, comprehensive summary (Other academic)
This thesis summarizes three novel and general reaction protocols for the synthesis of diaryliodonium salts. All protocols utilize mCPBA as oxidant and the acids used are either TfOH, to obtain triflate salts, or BF3•Et2O that gives the corresponding tetrafluoroborate salts in situ.
Chapter two describes the reaction of various arenes and aryl iodides, delivering electron-rich and electron-deficient triflates in moderate to excellent yields.
In chapter three, it is shown that the need of aryl iodides can be circumvented, as molecular iodine can be used together with arenes in a direct one-pot, three-step synthesis of symmetric diaryliodonium triflates.
The final and fourth chapter describes the development of a sequential one-pot reaction from aryl iodides and boronic acids, delivering symmetric and unsymmetric, electron-rich and electron-deficient iodonium tetrafluoroborates in moderate to excellent yields. This protocol was developed to overcome mechanistic limitations existing in the protocols described in chapter two and three.
The methodology described in this thesis is the most general, efficient and high-yielding existing up to date, making diaryliodonium salts easily available for various applications in synthesis.
Place, publisher, year, edition, pages
Stockholm: Department of Organic Chemistry, Stockholm University , 2008. , 49 p.
Hypervalent Iodine Compounds, One-Pot Synthesis, Regiospecific Synthesis, Aromatic Substitution, Aryl Iodides, Arenes, Boronic Acids
IdentifiersURN: urn:nbn:se:su:diva-7969ISBN: 978-91-7155-686-8OAI: oai:DiVA.org:su-7969DiVA: diva2:199372
2008-06-25, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 12 A, Stockholm, 10:00
Olofsson, Berit, Docent
List of papers