Literature DB >> 27560791

Xenon Difluoride Mediated Fluorodecarboxylations for the Syntheses of Di- and Trifluoromethoxyarenes.

Claire Chatalova-Sazepin1, Meruyert Binayeva1, Maxim Epifanov1, Wei Zhang1, Paul Foth1, Carolyn Amador1, Manu Jagdeo1, Benjamin R Boswell1, Glenn M Sammis1.   

Abstract

XeF2 is demonstrated to be a more proficient fluorine-transfer reagent than either NFSI or Selectfluor in fluorodecarboxylations of both mono- and difluoroaryloxy acetic acid derivatives. This method efficiently converts a wide range of neutral and electron-poor substrates to afford the desired di- and trifluoromethyl aryl ethers in good to excellent yields. The purifications are facile, and the reaction times are less than 5 min, which makes these fluorodecarboxylations promising for future PET-imaging applications.

Entities:  

Year:  2016        PMID: 27560791     DOI: 10.1021/acs.orglett.6b02208

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


  4 in total

1.  Decarboxylative Halogenation of Organic Compounds.

Authors:  Andrii Varenikov; Evgeny Shapiro; Mark Gandelman
Journal:  Chem Rev       Date:  2020-11-17       Impact factor: 60.622

2.  Late-Stage Conversion of a Metabolically Labile Aryl Methyl Ether-Containing Natural Product to Fluoroalkyl Analogues.

Authors:  Jacob P Sorrentino; Brett R Ambler; Ryan A Altman
Journal:  J Org Chem       Date:  2020-03-27       Impact factor: 4.354

3.  Trifluoromethyl Nonaflate: A Practical Trifluoromethoxylating Reagent and its Application to the Regio- and Stereoselective Synthesis of Trifluoromethoxylated Alkenes.

Authors:  Zhichao Lu; Tatsuya Kumon; Gerald B Hammond; Teruo Umemoto
Journal:  Angew Chem Int Ed Engl       Date:  2021-06-17       Impact factor: 16.823

4.  Selective C-H trifluoromethoxylation of (hetero)arenes as limiting reagent.

Authors:  Zhijie Deng; Mingxin Zhao; Feng Wang; Pingping Tang
Journal:  Nat Commun       Date:  2020-05-22       Impact factor: 14.919

  4 in total

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