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Trifluoromethanesulfonic acid in organic synthesis

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Abstract

The review analyzes data published in the past decade on the use of trifluoromethanesulfonic acid (triflic acid, CF3SO3H, TfOH) in organic synthesis, in particular in electrophilic aromatic substitution (Friedel–Crafts) reactions, formation of carbon–carbon and carbon–heteroatom bonds, isomerizations, syntheses of carboand heterocyclic structures, and other reactions, as well as in natural and organometallic compounds chemistry. The high protonating power and low nucleophilicity makes trifluoromethanesulfonic acid capable of generating from organic molecules cationic species which can be detected by spectral methods (NMR, IR spectroscopy, etc.), and their transformations can be studied. Experimental simplicity and efficiency of reactions promoted by trifluoromethanesulfonic acid make it a convenient reagent for the synthesis of new organic compounds.

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Authors and Affiliations

  1. St. Petersburg State University, Universitetskii pr. 26, St. Petersburg, 198504, Russia

    A. N. Kazakova & A. V. Vasilyev

  2. St. Petersburg State Forest Technical University, Institutskii per. 5, St. Petersburg, 194021, Russia

    A. V. Vasilyev

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Original Russian Text © A.N. Kazakova, A.V. Vasilyev, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 4, pp. 479–502.

Anna Nikolaevna Kazakova was born in 1985 in Sterlitamak. In 2008 she graduated from the Sterlitamak State Pedagogical Academy and in 2011 finished post-graduate courses at the Ufa State Petroleum Technological University. Candidate of chemical sciences. Since 2013 she works as assistant at the Institute of Chemistry, St. Petersburg State University.

Fields of scientific interest: chemistry of halogen-substituted carbocations, synthesis and electrophilic reactions of organofluorine compounds.

Aleksandr Viktorovich Vasilyev was born in 1970 in Leningrad. In 1992 he graduated from the Faculty of Chemistry, St. Petersburg State University. Doctor of chemical sciences, director of the Institute of Chemical Processing of Wood Biomass and Technosphere Safety at the St. Petersburg State Forest Technical University, Head of the Chemistry Department of the St. Petersburg State Forest Technical University, Professor at the Organic Chemistry Department of the St. Petersburg State University.

Fields of scientific interest: electrophilic activation of organic compounds, chemistry of unsaturated compounds, new methods of carbon–carbon bond formation, chemistry of organofluorine compounds, organic synthesis based on natural compounds.

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Kazakova, A.N., Vasilyev, A.V. Trifluoromethanesulfonic acid in organic synthesis. Russ J Org Chem 53, 485–509 (2017). https://doi.org/10.1134/S1070428017040017

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