Literature DB >> 26450682

Hypervalent Iodine-Mediated Fluorination of Styrene Derivatives: Stoichiometric and Catalytic Transformation to 2,2-Difluoroethylarenes.

Tsugio Kitamura1, Kensuke Muta1, Juzo Oyamada1.   

Abstract

Fluorination of styrene derivatives with a reagent system composed of μ-oxo-bis[trifluoroacetato(phenyl)iodine] and a pyridine·HF complex gave the corresponding (2,2-difluoroethyl)arenes in good yields. Similarly, the reagent of PhI(OCOCF3)2 and the pyridine·HF complex acted as a fluorinating agent for styrene derivatives. The fluorination of styrene derivatives with the pyridine·HF complex underwent under catalytic conditions using 4-iodotoluene as a catalyst and m-CPBA as a terminal oxidant.

Entities:  

Year:  2015        PMID: 26450682     DOI: 10.1021/acs.joc.5b01929

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


  16 in total

1.  Catalytic, Enantioselective 1,2-Difluorination of Cinnamamides.

Authors:  Moriana K Haj; Steven M Banik; Eric N Jacobsen
Journal:  Org Lett       Date:  2019-04-09       Impact factor: 6.005

2.  Enantioselective, Catalytic Fluorolactonization Reactions with a Nucleophilic Fluoride Source.

Authors:  Eric M Woerly; Steven M Banik; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2016-10-13       Impact factor: 15.419

3.  Mechanism and Origins of Chemo- and Stereoselectivities of Aryl Iodide-Catalyzed Asymmetric Difluorinations of β-Substituted Styrenes.

Authors:  Biying Zhou; Moriana K Haj; Eric N Jacobsen; K N Houk; Xiao-Song Xue
Journal:  J Am Chem Soc       Date:  2018-11-05       Impact factor: 15.419

4.  Catalytic, asymmetric difluorination of alkenes to generate difluoromethylated stereocenters.

Authors:  Steven M Banik; Jonathan William Medley; Eric N Jacobsen
Journal:  Science       Date:  2016-07-01       Impact factor: 47.728

5.  Catalytic, Diastereoselective 1,2-Difluorination of Alkenes.

Authors:  Steven M Banik; Jonathan William Medley; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2016-04-12       Impact factor: 15.419

6.  Trifluorinated Tetralins via I(I)/I(III)-Catalysed Ring Expansion: Programming Conformation by [CH2 CH2 ] → [CF2 CHF] Isosterism.

Authors:  Jessica Neufeld; Timo Stünkel; Christian Mück-Lichtenfeld; Constantin G Daniliuc; Ryan Gilmour
Journal:  Angew Chem Int Ed Engl       Date:  2021-05-01       Impact factor: 15.336

7.  Fluorinative ring-opening of cyclopropanes by hypervalent iodine reagents. An efficient method for 1,3-oxyfluorination and 1,3-difluorination.

Authors:  Nadia O Ilchenko; Martin Hedberg; Kálmán J Szabó
Journal:  Chem Sci       Date:  2016-09-16       Impact factor: 9.825

Review 8.  Recent advances in hypervalent iodine(III)-catalyzed functionalization of alkenes.

Authors:  Xiang Li; Pinhong Chen; Guosheng Liu
Journal:  Beilstein J Org Chem       Date:  2018-07-18       Impact factor: 2.883

9.  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

10.  Rhodium-Catalyzed Geminal Oxyfluorination and Oxytrifluoro-Methylation of Diazocarbonyl Compounds.

Authors:  Weiming Yuan; Lars Eriksson; Kálmán J Szabó
Journal:  Angew Chem Int Ed Engl       Date:  2016-05-24       Impact factor: 15.336

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