Literature DB >> 20163086

A general and convenient preparation of [bis(trifluoroacetoxy)iodo]perfluoroalkanes and [bis(trifluoroacetoxy)iodo]arenes by oxidation of organic iodides using oxone and trifluoroacetic acid.

Aleksandra A Zagulyaeva1, Mekhman S Yusubov, Viktor V Zhdankin.   

Abstract

[Bis(trifluoroacetoxy)iodo]perfluoroalkanes C(n)F(2n+1)I(OCOCF(3))(2) (n = 4, 6, 8, 10, 12) can be conveniently prepared by the oxidation of the corresponding perfluoroalkyl iodides with Oxone in trifluoroacetic acid at room temperature and subsequently converted to the stable [hydroxy(tosyloxy)iodo]perfluoroalkanes, C(n)F(2n+1)I(OH)OTs, by treatment with p-toluenesulfonic acid. This general and convenient procedure has been further extended to the synthesis of various [bis(trifluoroacetoxy)iodo]arenes, ArI(OCOCF(3))(2).

Entities:  

Year:  2010        PMID： 20163086     DOI： 10.1021/jo902733f

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  11 in total

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4.  Facile One-Pot Synthesis of Diaryliodonium Salts from Arenes and Aryl Iodides with Oxone.

Authors:  Natalia Soldatova; Pavel Postnikov; Olga Kukurina; Viktor V Zhdankin; Akira Yoshimura; Thomas Wirth; Mekhman S Yusubov
Journal:  ChemistryOpen       Date:  2016-12-16       Impact factor: 2.911

5.  Syntheses, structures, and stabilities of aliphatic and aromatic fluorous iodine(I) and iodine(III) compounds: the role of iodine Lewis basicity.

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Journal:  Beilstein J Org Chem       Date:  2017-11-23       Impact factor: 2.883

6.  Electrochemical-Induced Ring Transformation of Cyclic α-(ortho-Iodophenyl)-β-oxoesters.

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Journal:  Chemistry       Date:  2020-01-30       Impact factor: 5.236

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Authors:  Jannis Ludwig; Tobias Moje; Fynn Röhricht; Rainer Herges
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8.  Mechanistic Studies and Radiofluorination of Structurally Diverse Pharmaceuticals with Spirocyclic Iodonium(III) Ylides.

Authors:  Benjamin H Rotstein; Lu Wang; Richard Y Liu; Jon Patteson; Eugene E Kwan; Neil Vasdev; Steven H Liang
Journal:  Chem Sci       Date:  2016-03-24       Impact factor: 9.825

9.  One-pot synthesis of diaryliodonium salts from arenes and aryl iodides with Oxone-sulfuric acid.

Authors:  Natalia Soldatova; Pavel Postnikov; Olga Kukurina; Viktor V Zhdankin; Akira Yoshimura; Thomas Wirth; Mekhman S Yusubov
Journal:  Beilstein J Org Chem       Date:  2018-04-12       Impact factor: 2.883

10.  ¹⁷O-Dynamic NMR and DFT investigation of bis(acyloxy)iodoarenes.

Authors:  Luca Fusaro; Francesca Mocci; Michel Luhmer; Giovanni Cerioni
Journal:  Molecules       Date:  2012-10-26       Impact factor: 4.411
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