Literature DB >> 19142916

Palladium-catalyzed substitution of allylic fluorides.

Amaruka Hazari1, Véronique Gouverneur, John M Brown.   

Abstract

As unusual substrates for the Tsuji-Trost allylation reaction, allylic fluorides are responsive to palladium-catalyzed substitution. Their activity towards this reaction fits in the series OCO(2)Me>OBz>>F>>OAc. The classic stereoretention mechanism that involves sequential inversions does not operate in this case. Several distinct cases are considered.

Entities:  

Year:  2009        PMID： 19142916     DOI： 10.1002/anie.200804310

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


  5 in total

1.  Catalytic Nucleophilic Fluorination of Secondary and Tertiary Propargylic Electrophiles with a Copper-N-Heterocyclic Carbene Complex.

Authors:  Li-Jie Cheng; Christopher J Cordier
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-25       Impact factor: 15.336

2.  Highly selective nickel-catalyzed gem-difluoropropargylation of unactivated alkylzinc reagents.

Authors:  Lun An; Chang Xu; Xingang Zhang
Journal:  Nat Commun       Date:  2017-11-13       Impact factor: 14.919

3.  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

4.  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

Review 5.  Closing the gap between 19F and 18F chemistry.

Authors:  Javier Ajenjo; Gianluca Destro; Bart Cornelissen; Véronique Gouverneur
Journal:  EJNMMI Radiopharm Chem       Date:  2021-09-25
  5 in total

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