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Base- and Additive-Free Ir-Catalyzed ortho-Iodination of Benzoic Acids: Scope and Mechanistic Investigations
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0003-1331-9283
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0002-1729-598X
Stockholm University, Faculty of Science, Department of Organic Chemistry.
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2018 (English)In: ACS Catalysis, ISSN 2155-5435, E-ISSN 2155-5435, Vol. 8, no 2, p. 920-925Article in journal (Refereed) Published
Abstract [en]

A protocol for the C-H activation/iodination of benzoic acids catalyzed by a simple iridium complex has been developed. The method described in this paper allows the ortho-selective iodination of a variety of benzoic acids under extraordinarily mild conditions in the absence of any additive or base in 1,1,1,3,3,3-hexafluoroisopropanol as the solvent. The iridium catalyst used tolerates air and moisture, and selectively gives ortho-iodobenzoic acids with high conversions. Mechanistic investigations revealed that an Ir(III)/Ir(V) catalytic cycle operates, and that the unique properties of HFIP enables the C-H iodination using the carboxylic moiety as a directing group.

Place, publisher, year, edition, pages
2018. Vol. 8, no 2, p. 920-925
Keywords [en]
C-H iodination, benzoic acids, iridium catalysis, 1, 1, 1, 3, 3, 3-hexafluoroisopropanol, hydrogen bonding
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-153631DOI: 10.1021/acscatal.7b02987ISI: 000424735000022OAI: oai:DiVA.org:su-153631DiVA, id: diva2:1189850
Funder
Swedish Research CouncilSwedish Research Council FormasKnut and Alice Wallenberg FoundationAvailable from: 2018-03-13 Created: 2018-03-13 Last updated: 2018-10-24Bibliographically approved
In thesis
1. Development of New Efficient Iridium-Catalyzed Methods for the Construction of Carbon-Heteroatom Bonds
Open this publication in new window or tab >>Development of New Efficient Iridium-Catalyzed Methods for the Construction of Carbon-Heteroatom Bonds
2018 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Today’s society has a large demand for biologically active chemicals that can be used for example as pharmaceuticals and in the agriculture. These are normally constructed by assembling together several smaller chemical molecules. In order to achieve this, we need that these small molecules contain certain reactive sites, or in other words, that they are functionalized with certain atoms. The work in this thesis investigates and develops new methods to create functionalities in molecules, which in turn can be used to construct larger compounds and other materials important for our society.

 The methods herein developed are based on the use of metal catalysts to construct carbon-halogen bonds. Examples of halogens include bromide and iodide. When a molecule contains one (or more) of these bonds, it can be transformed in a simple chemical step into other compounds. The number of possible chemical transformations becomes almost endless. Thus, by accessing these compounds, chemical libraries can be created easily.

Throughout the work, sustainability has been prioritized by using, for the human health, friendly solvents whenever possible, by using versatile, stable and structurally simple but yet effective catalysts, and by minimizing the need to use unnecessary chemical activators.

Place, publisher, year, edition, pages
Stockholm: Department of Organic Chemistry, Stockholm University, 2018. p. 68
Keywords
Iridium Catalysis, Method development, Halogenation, Isomerization, C-H Activation
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-161412 (URN)978-91-7797-486-4 (ISBN)978-91-7797-487-1 (ISBN)
Public defence
2018-12-10, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 16 B, Stockholm, 10:00 (English)
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Supervisors
Note

At the time of the doctoral defense, the following paper was unpublished and had a status as follows: Paper 4: Manuscript.

Available from: 2018-11-15 Created: 2018-10-24 Last updated: 2018-12-13Bibliographically approved

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