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HomeWebinarsNovel Reactivity in Hypervalent Iodine-Mediated Arylations and Vinylations

Novel Reactivity in Hypervalent Iodine-Mediated Arylations and Vinylations



WEBINAR

The lecture will focus on our recently developed diarylation cascade methodology yielding diaryl ethers, diarylamines and triarylamines with excellent atom economy. In this reaction, both aryl groups in diaryliodonium salts are efficiently transferred to amines and water under mild and transition metal-free conditions. The reaction follows a novel mechanistic pathway with initial nucleophilic aromatic substitution and a subsequent intramolecular aryl transfer.

The chemistry of our recently discovered hypervalent iodine(III) reagents vinylbenziodoxolones (VBX) will also be presented. This compound class is an efficient vinylating agent with various nucleophiles under mild conditions, without need for a transition metal catalyst or excess reagents. Interestingly, internal or terminal alkene products are regioselectively formed, depending on the nucleophile. Our results in the C-vinylation of nitroalkanes, P-vinylation of phosphine oxides and H-phosphinates and S-vinylation of thiols and mercaptothiazoles will be discussed, together with a mechanistic study to rationalize the regio- and stereoselectivity.

Learning points:

  • Learn the chemistry of recently discovered hypervalent iodine(III) reagents vinylbenziodoxolones (VBX)
  • Learn how the hypervalent Iodine (III) reagent perform in diarylation cascade methodology yielding diaryl ethers, diarylamines and triarylamines with excellent atom economy

 

Speakers

Berit Olofsson

Berit Olofsson

Stockholm University, Sweden

Dean of Chemistry

Prof. Berit Olofsson has a PhD from in synthetic organic chemistry from KTH, Stockholm, Sweden in 2002. She conducted post doctoral studies at Bristol University, UK with Prof. Aggarwal in 2003-2004. Returning to Sweden, she became assistant supervisor in the group of Prof. Bäckvall at Stockholm University (SU). She started her independent career as Assistant Professor at SU in 2006, focusing on hypervalent iodine chemistry. After some years as Associate Professor, she was promoted to Full Professor in 2013. Since 2019, she also serves as the Dean of Chemistry.
Selected commissions of trust: Secretary of the Division of organic chemistry at EuChemS, Member of the international advisory board of Angew. Chemie, Chair of the board of SUCCeSS (tockholm university center for circular and sustainable systems).

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