Literature DB >> 22594918

Palladium-catalyzed substitution and cross-coupling of benzylic fluorides.

George Blessley1, Patrick Holden, Matthew Walker, John M Brown, Véronique Gouverneur.   

Abstract

Benzylic fluorides are suitable substrates for Pd(0)-catalyzed Tsuji-Trost substitution using carbon, nitrogen, oxygen, and sulfur nucleophiles and for cross-coupling with phenylboronic acid. For the bifunctional substrate 4-chlorobenzyl fluoride, fine-tuning of the reaction conditions allows for the regioselective displacement of either the chlorine or fluorine substituent. The leaving group ability of fluoride vs other groups displaced in substitution is CF(3)CO(2) ≈ p-NO(2)C(6)H(4)CO(2) ≈ OCO(2)CH(3) > F > CH(3)CO(2), a ranking similar to allylic fluorides under Pd catalysis.

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Year:  2012        PMID： 22594918     DOI： 10.1021/ol300977f

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


  8 in total

1.  Palladium and Nickel Catalyzed Suzuki Cross-Coupling with Alkyl Fluorides.

Authors:  Kaluvu Balaraman; Christian Wolf
Journal:  Org Lett       Date:  2021-11-01       Impact factor: 6.005

2.  Nickel-catalyzed cross couplings of benzylic ammonium salts and boronic acids: stereospecific formation of diarylethanes via C-N bond activation.

Authors:  Prantik Maity; Danielle M Shacklady-McAtee; Glenn P A Yap; Eric R Sirianni; Mary P Watson
Journal:  J Am Chem Soc       Date:  2012-12-26       Impact factor: 15.419

3.  Copper-Catalyzed C-H Fluorination/Functionalization Sequence Enabling Benzylic C-H Cross Coupling with Diverse Nucleophiles.

Authors:  Aristidis Vasilopoulos; Dung L Golden; Joshua A Buss; Shannon S Stahl
Journal:  Org Lett       Date:  2020-07-29       Impact factor: 6.005

4.  DFT Studies on Ni-Mediated C-F Cleavage for the Synthesis of Cyclopentadiene Derivatives.

Authors:  Wen-Jie Chen; Ruo-Nan Xu; Weimin Lin; Xuejiao Sun; Bin Wang; Qi-Hui Wu; Xin Huang
Journal:  Front Chem       Date:  2018-08-13       Impact factor: 5.221

5.  Desymmetrization of difluoromethylene groups by C-F bond activation.

Authors:  Trevor W Butcher; Jonathan L Yang; Willi M Amberg; Nicholas B Watkins; Natalie D Wilkinson; John F Hartwig
Journal:  Nature       Date:  2020-06-01       Impact factor: 49.962

6.  Catalytic stereospecific allyl-allyl cross-coupling of internal allyl electrophiles with AllylB(pin).

Authors:  Hai Le; Amanda Batten; James P Morken
Journal:  Org Lett       Date:  2014-04-04       Impact factor: 6.005

7.  Triol-promoted activation of C-F bonds: Amination of benzylic fluorides under highly concentrated conditions mediated by 1,1,1-tris(hydroxymethyl)propane.

Authors:  Pier Alexandre Champagne; Alexandre Saint-Martin; Mélina Drouin; Jean-François Paquin
Journal:  Beilstein J Org Chem       Date:  2013-11-13       Impact factor: 2.883

8.  Organophotoredox Hydrodefluorination of Trifluoromethylarenes with Translational Applicability to Drug Discovery.

Authors:  Jeroen B I Sap; Natan J W Straathof; Thomas Knauber; Claudio F Meyer; Maurice Médebielle; Laura Buglioni; Christophe Genicot; Andrés A Trabanco; Timothy Noël; Christopher W Am Ende; Véronique Gouverneur
Journal:  J Am Chem Soc       Date:  2020-05-11       Impact factor: 15.419
  8 in total

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