Literature DB >> 25393744

AgF-mediated fluorinative cross-coupling of two olefins: facile access to α-CF3 alkenes and β-CF3 ketones.

Bing Gao1, Yanchuan Zhao, Jinbo Hu.   

Abstract

A AgF-mediated fluorination with a concomitant cross-coupling between a gem-difluoroolefin and a non-fluorinated olefin is reported. This highly efficient method provides facile access to both α-CF3 alkenes and β-CF3 ketones, which otherwise remain challenging to be directly prepared. The application of this method is further demonstrated by the synthesis of bioactive isoxazoline derivatives. This approach represents a conceptually novel route to trifluoromethylated compounds that combines the in situ generation of the CF3 moiety and a C-H functionalization in a single reaction system.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkenes; fluorination; fluorine; ketones; silver

Mesh:

Substances:

Year:  2014        PMID: 25393744     DOI: 10.1002/anie.201409705

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  7 in total

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2.  Cu(II)-Catalyzed Unsymmetrical Dioxidation of gem-Difluoroalkenes to Generate α,α-Difluorinated-α-phenoxyketones.

Authors:  Suvajit Koley; Kaylee T Cayton; Gisela A González-Montiel; M Ramu Yadav; Douglas L Orsi; Andrew J Intelli; Paul Ha-Yeon Cheong; Ryan A Altman
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3.  Cobalt-Catalyzed Selective Unsymmetrical Dioxidation of gem-Difluoroalkenes.

Authors:  Douglas L Orsi; Justin T Douglas; Jacob P Sorrentino; Ryan A Altman
Journal:  J Org Chem       Date:  2020-08-05       Impact factor: 4.354

4.  Efficient Synthesis of β-CF3/SCF3-Substituted Carbonyls via Copper-Catalyzed Electrophilic Ring-Opening Cross-Coupling of Cyclopropanols.

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6.  Synthesis of bioactive fluoropyrrolidines via copper(i)-catalysed asymmetric 1,3-dipolar cycloaddition of azomethine ylides.

Authors:  Xiao Xu; Longzhu Bao; Lu Ran; Zhenyan Yang; Dingce Yan; Chun-Jiang Wang; Huailong Teng
Journal:  Chem Sci       Date:  2021-12-07       Impact factor: 9.825

7.  Acid-Catalyzed Hydrothiolation of gem-Difluorostyrenes to Access α,α-Difluoroalkylthioethers.

Authors:  Jacob P Sorrentino; Douglas L Orsi; Ryan A Altman
Journal:  J Org Chem       Date:  2021-01-20       Impact factor: 4.354

  7 in total

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