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Efficient and High-Yielding Routes to Diaryliodonium Salts
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Responsible organisation
2008 (English)Licentiate thesis, comprehensive summary (Other academic)
Abstract [en]

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.
Keyword [en]
Hypervalent Iodine Compounds, One-Pot Synthesis, Regiospecific Synthesis, Aromatic Substitution, Aryl Iodides, Arenes, Boronic Acids
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-7969ISBN: 978-91-7155-686-8 (print)OAI: oai:DiVA.org:su-7969DiVA: diva2:199372
Presentation
2008-06-25, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 12 A, Stockholm, 10:00
Supervisors
Available from: 2008-06-16 Created: 2008-06-16 Last updated: 2011-03-17Bibliographically approved
List of papers
1. High-Yielding One-Pot Synthesis of Diaryliodonium Triflates from Arenes and Iodine or Aryl Iodides
Open this publication in new window or tab >>High-Yielding One-Pot Synthesis of Diaryliodonium Triflates from Arenes and Iodine or Aryl Iodides
2007 (English)In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, no 24, 2521-2523 p.Article in journal (Refereed) Published
Abstract [en]

Unsymmetric and symmetric diaryliodonium triflates are synthesized from both electron-deficient and electron-rich substrates in a fast, high yielding, and operationally simple protocol employing arenes and aryl iodides or iodine.

National Category
Inorganic Chemistry Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-25299 (URN)10.1039/b701864a (DOI)
Available from: 2008-06-16 Created: 2008-06-16 Last updated: 2015-03-21Bibliographically approved
2. Efficient and General One-Pot Synthesis of Diaryliodonium Triflates: Optimization, Scope and Limitations
Open this publication in new window or tab >>Efficient and General One-Pot Synthesis of Diaryliodonium Triflates: Optimization, Scope and Limitations
2007 (English)In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 349, no 17-18, 2610-2618 p.Article in journal (Refereed) Published
Abstract [en]

Symmetrical and unsymmetrical diaryliodonium triflates have been synthesized from both electron-deficient and electron-rich arenes and aryl iodides with mCPBA and triflic acid. A thorough investigation of the optimization, scope and limitations has resulted in an improved one-pot protocol that is fast, high-yielding, and operationally simple. The reaction has been extended to the direct synthesis of symmetrical iodonium salts from iodine and arenes, conveniently circumventing the need for aryl iodides.

Keyword
arenes, aromatic substitution, diaryliodonium salts, hypervalent compounds, iodine, oxidation
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-25300 (URN)10.1002/adsc.200700373 (DOI)000251737500011 ()
Funder
Swedish Research Council, 621-2006-4027
Available from: 2008-06-16 Created: 2008-06-16 Last updated: 2015-10-13Bibliographically approved
3. Regiospecific One-Pot Synthesis of Diaryliodonium Tetrafluoroborates from Arylboronic Acids and Aryl Iodides
Open this publication in new window or tab >>Regiospecific One-Pot Synthesis of Diaryliodonium Tetrafluoroborates from Arylboronic Acids and Aryl Iodides
2008 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 73, no 12, 4602-4607 p.Article in journal (Refereed) Published
Abstract [en]

Diaryliodonium salts have recently received considerable attention as mild arylation reagents in organic synthesis. This paper describes a regiospecific, sequential one-pot synthesis of symmetrical and unsymmetrical diaryliodonium tetrafluoroborates, which are the most popular salts in metal-catalyzed arylations. The protocol is fast and high-yielding and has a large substrate scope. Furthermore, the corresponding diaryliodonium triflates can conveniently be obtained via an in situ anion exchange.

Keyword
diaryliodonium salts, MCPBA
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-25301 (URN)10.1021/jo8004974 (DOI)000256757100030 ()
Funder
Swedish Research Council, 621-2006-4027
Available from: 2008-06-16 Created: 2008-06-16 Last updated: 2015-10-27Bibliographically approved

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