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Metal-Free C-Arylation of Nitro Compounds with Diaryliodonium Salts
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi. Wallenberg Research Centre at Stellenbosch University, South Africa.
2015 (Engelska)Ingår i: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 17, nr 18, s. 4554-4557Artikel i tidskrift (Refereegranskat) Published
Abstract [en]

An efficient, mild, and metal-free arylation of nitro-alkanes with diaryliodonium salts has been developed, giving easy access to tertiary nitro compounds. The reaction proceeds in high yields without the need for excess reagents and can be extended to alpha-arylation of nitroesters. Nitroalkanes were selectively C-arylated in the presence of other easily arylated functional groups, such as phenols and aliphatic alcohols.

Ort, förlag, år, upplaga, sidor
2015. Vol. 17, nr 18, s. 4554-4557
Nationell ämneskategori
Organisk kemi
Forskningsämne
organisk kemi
Identifikatorer
URN: urn:nbn:se:su:diva-122329DOI: 10.1021/acs.orglett.5b02270ISI: 000361867800040OAI: oai:DiVA.org:su-122329DiVA, id: diva2:875283
Forskningsfinansiär
Carl Tryggers stiftelse för vetenskaplig forskning Tillgänglig från: 2015-12-01 Skapad: 2015-10-29 Senast uppdaterad: 2017-12-01Bibliografiskt granskad
Ingår i avhandling
1. Metal-Free O- and C-Arylation with Diaryliodonium Salts
Öppna denna publikation i ny flik eller fönster >>Metal-Free O- and C-Arylation with Diaryliodonium Salts
2017 (Engelska)Doktorsavhandling, sammanläggning (Övrigt vetenskapligt)
Abstract [en]

This thesis concerns the development of metal-free applications using diaryliodonium salts. The first project describes an arylation protocol of allylic and benzylic alcohols in aqueous media. The method proceeds under mild conditions and the ether products were obtained in moderate to good yields. The methodology was also expanded to include arylation of phenols, giving diaryl ethers in good to excellent yields. In the second project, an arylation method that included a wider range of aliphatic alcohols was developed. The scope of accessible alkyl aryl ethers was studied and included a comparative study of phenylation and nitrophenylation of various alcohols. Finally, a formal metal-free synthesis of butoxycain was performed, illustrating the applicability of the developed method.

The third project focused on the limitations and side reactions occurring in Chapter 2 and 3. First, an approach to access symmetric diaryl ethers via arylation of hydroxide was presented. This reaction gave rise to a number of side products, which we hypothesized to originate from aryne-type intermediates. A mechanism for the formation of these side products was suggested, supported by trapping and deuterium labeling experiments.

Oxidation of the alcohol to the corresponding ketone was also observed and the mechanism of this interesting side reaction was investigated. The latter was suggested to proceed via an intramolecular oxidation without the involvement of radicals or arynes.

The fourth project covers a method to synthesize highly sterically congested alkyl aryl ethers via arylation of tertiary alcohols using diaryliodonium salts. The method displayed a broad scope of tertiary alcohols and was also suitable for fluorinated alcohols.

The final project detailed in this thesis deals with C-arylation with diaryliodonium salts, showcasing nitroalkanes as well as a nitro ester as suitable nucleophiles for metal-free arylation. 

Ort, förlag, år, upplaga, sidor
Stockholm: Department of Organic Chemistry, Stockholm University, 2017. s. 85
Nyckelord
Hypervalent Iodine, Alkyl Aryl Ethers, Nitro Compounds, Alcohols, Diaryliodonium Salts
Nationell ämneskategori
Organisk kemi
Forskningsämne
organisk kemi
Identifikatorer
urn:nbn:se:su:diva-140944 (URN)978-91-7649-702-9 (ISBN)978-91-7649-703-6 (ISBN)
Disputation
2017-05-12, Magnélisalen, Kemiska Övningslaboratoriet, Svante Arrhenius väg 16 B, Stockholm, 10:00 (Engelska)
Opponent
Handledare
Anmärkning

At the time of the doctoral defense, the following paper was unpublished and had a status as follows: Paper 3: Manuscript.

Tillgänglig från: 2017-04-19 Skapad: 2017-03-24 Senast uppdaterad: 2018-02-20Bibliografiskt granskad

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