Literature DB >> 21473585

A practical and convenient fluorination of 1,3-dicarbonyl compounds using aqueous HF in the presence of iodosylbenzene.

Tsugio Kitamura1, Satoshi Kuriki, Mohammad Hasan Morshed, Yuji Hori.   

Abstract

A simple, practical, and convenient fluorination of 1,3-dicarbonyl compounds was achieved by direct use of aqueous hydrofluoric acid and iodosylbenzene (PhIO). The reaction of ethyl benzoylacetate with the reagent system of aqueous HF and PhIO in CH(2)Cl(2) gave ethyl 2-fluoro-2-benzolyacetate in 98% yield. Other 1,3-dicarbonyl compounds including β-keto esters and 1,3-diketones underwent the fluorination reaction to give the corresponding fluorinated products in good yields.

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Year:  2011        PMID: 21473585     DOI: 10.1021/ol200632d

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  7 in total

1.  Gold-catalyzed Fluorination of Alkynyl Esters and Ketones: Efficient Access to Fluorinated 1,3-Dicarbonyl Compounds.

Authors:  Xiaojun Zeng; Zhichao Lu; Shiwen Liu; Gerald B Hammond; Bo Xu
Journal:  Adv Synth Catal       Date:  2017-10-05       Impact factor: 5.837

2.  Mild silver-mediated geminal difluorination of styrenes using an air- and moisture-stable fluoroiodane reagent.

Authors:  Nadia O Ilchenko; Boris O A Tasch; Kálmán J Szabó
Journal:  Angew Chem Int Ed Engl       Date:  2014-10-21       Impact factor: 15.336

3.  Reaction of iodonium ylides of 1,3-dicarbonyl compounds with HF reagents.

Authors:  Keisuke Gondo; Tsugio Kitamura
Journal:  Molecules       Date:  2012-05-31       Impact factor: 4.411

Review 4.  Kitamura Electrophilic Fluorination Using HF as a Source of Fluorine.

Authors:  Jianlin Han; Greg Butler; Hiroki Moriwaki; Hiroyuki Konno; Vadim A Soloshonok; Tsugio Kitamura
Journal:  Molecules       Date:  2020-04-30       Impact factor: 4.411

Review 5.  Recent discoveries on the structure of iodine(iii) reagents and their use in cross-nucleophile coupling.

Authors:  Adriano Bauer; Nuno Maulide
Journal:  Chem Sci       Date:  2021-01-07       Impact factor: 9.825

6.  Flow electrochemistry: a safe tool for fluorine chemistry.

Authors:  Bethan Winterson; Tim Rennigholtz; Thomas Wirth
Journal:  Chem Sci       Date:  2021-06-04       Impact factor: 9.825

7.  A Novel Synthesis of 4-Acetoxyl 5(4H)-Oxazolones by Direct α-Oxidation of N-Benzoyl Amino-Acid Using Hypervalent Iodine.

Authors:  Gang Wen; Wen-Xuan Zhang; Song Wu
Journal:  Molecules       Date:  2017-07-03       Impact factor: 4.411

  7 in total

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