Synthesis of Multifunctional Aryl(trifloxyalkenyl)iodonium Triflate Salts

Balázs L Tóth; Ferenc Béke; Orsolya Egyed; Attila Bényei; András Stirling; Zoltán Novák

doi:10.1021/acsomega.9b00728

Synthesis of Multifunctional Aryl(trifloxyalkenyl)iodonium Triflate Salts

ACS Omega. 2019 May 24;4(5):9188-9197. doi: 10.1021/acsomega.9b00728. eCollection 2019 May 31.

Authors

Balázs L Tóth¹, Ferenc Béke¹, Orsolya Egyed², Attila Bényei³, András Stirling², Zoltán Novák¹

Affiliations

¹ ELTE "Lendület" Catalysis and Organic Synthesis Research Group, Institute of Chemistry, Eötvös Loránd University, Faculty of Science, Pázmány Péter stny. 1/A, H-1117 Budapest, Hungary.
² Research Centre for Natural Sciences of the Hungarian Academy of Sciences, Magyar Tudósok körútja 2, H-1117 Budapest, Hungary.
³ Department of Pharmaceutical Chemistry, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary.

Abstract

A convenient procedure for the synthesis of aryl(trifloxyalkenyl)iodonium triflate salts from commercially available (diacetoxyiodo)benzene, trimethylsilyl trifluoromethanesulfonate, and acetylenes under mild conditions was developed. The obtained multifunctional hypervalent vinyliodonium salts equipped with electrophilic and nucleophilic functions could serve as novel C2 synthons for organic transformations. The structure of the iodonium salts was identified by multidimensional NMR spectroscopy and X-ray crystallography.