Literature DB >> 19809621

Acid-mediated formation of trifluoromethyl sulfonates from sulfonic acids and a hypervalent iodine trifluoromethylating agent.

Raffael Koller1, Quentin Huchet, Philip Battaglia, Jan M Welch, Antonio Togni.   

Abstract

A variety of sulfonic acids have been trifluoromethylated using 1-trifluoromethyl-1,2-benziodoxol-3(1H)-one under mild conditions in good to excellent yields. Initial mechanistic investigations of this reaction show a clean second-order kinetics and only very weak substrate electronic effects.

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Year:  2009        PMID: 19809621     DOI: 10.1039/b913962a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  10 in total

1.  Asymmetric silver-catalysed intermolecular bromotrifluoromethoxylation of alkenes with a new trifluoromethoxylation reagent.

Authors:  Shuo Guo; Fei Cong; Rui Guo; Liang Wang; Pingping Tang
Journal:  Nat Chem       Date:  2017-01-23       Impact factor: 24.427

2.  Copper-catalyzed trifluoromethylation of unactivated olefins.

Authors:  Andrew T Parsons; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2011-08-25       Impact factor: 15.336

3.  Iron(II)-catalyzed trifluoromethylation of potassium vinyltrifluoroborates.

Authors:  Andrew T Parsons; Todd D Senecal; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2012-02-10       Impact factor: 15.336

4.  Shelf-stable electrophilic trifluoromethylating reagents: A brief historical perspective.

Authors:  Norio Shibata; Andrej Matsnev; Dominique Cahard
Journal:  Beilstein J Org Chem       Date:  2010-06-16       Impact factor: 2.883

5.  The dual role of thiourea in the thiotrifluoromethylation of alkenes.

Authors:  Paolo Ricci; Tanatorn Khotavivattana; Lukas Pfeifer; Maurice Médebielle; John Richard Morphy; Véronique Gouverneur
Journal:  Chem Sci       Date:  2016-09-30       Impact factor: 9.825

6.  Synthesis of trifluoromethylated 2H-azirines through Togni reagent-mediated trifluoromethylation followed by PhIO-mediated azirination.

Authors:  Jiyun Sun; Xiaohua Zhen; Huaibin Ge; Guangtao Zhang; Xuechan An; Yunfei Du
Journal:  Beilstein J Org Chem       Date:  2018-06-15       Impact factor: 2.883

7.  Metal-free, visible-light induced enantioselective three-component dicarbofunctionalization and oxytrifluoromethylation of enamines via chiral phosphoric acid catalysis.

Authors:  Hui Liang; Dong-Sheng Ji; Guo-Qiang Xu; Yong-Chun Luo; Haixue Zheng; Peng-Fei Xu
Journal:  Chem Sci       Date:  2022-01-04       Impact factor: 9.825

8.  Isolation and Reactivity of Trifluoromethyl Iodonium Salts.

Authors:  Johnathan N Brantley; Andrew V Samant; F Dean Toste
Journal:  ACS Cent Sci       Date:  2016-05-13       Impact factor: 14.553

9.  Trifluoromethoxypyrazines: Preparation and Properties.

Authors:  Taras M Sokolenko; Yurii L Yagupolskii
Journal:  Molecules       Date:  2020-05-09       Impact factor: 4.411

10.  Merging hypervalent iodine and sulfoximine chemistry: a new electrophilic trifluoromethylation reagent.

Authors:  Jorna Kalim; Thibaut Duhail; Thanh-Nghi Le; Nicolas Vanthuyne; Elsa Anselmi; Antonio Togni; Emmanuel Magnier
Journal:  Chem Sci       Date:  2019-09-27       Impact factor: 9.825

  10 in total

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