Literature DB >> 27312982

Single C-F Bond Cleavage of Trifluoromethylarenes with an ortho-Silyl Group.

Suguru Yoshida1, Ken Shimomori2, Youngchan Kim2, Takamitsu Hosoya3.   

Abstract

The transformation of a single C-F bond of trifluoromethylarenes bearing a hydrosilyl group at the ortho position was achieved. The activation of the hydrosilyl group with a trityl cation in the presence of nucleophiles allowed for selective C-F bond functionalization, for example, by allylation, carboxylation, or chlorination. Further derivatization of the resulting fluorosilylarenes afforded various aromatic difluoromethylene compounds.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−F Activation; allylation; fluorine; silanes; trityl cation

Year:  2016        PMID： 27312982     DOI： 10.1002/anie.201604776

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


  10 in total

1.  Selective C-F Functionalization of Unactivated Trifluoromethylarenes.

Authors:  David B Vogt; Ciaran P Seath; Hengbin Wang; Nathan T Jui
Journal:  J Am Chem Soc       Date:  2019-08-09       Impact factor: 15.419

2.  Catalytic Enantioselective and Diastereoselective Allylic Alkylation with Fluoroenolates: Efficient Access to C3-Fluorinated and All-Carbon Quaternary Oxindoles.

Authors:  Kaluvu Balaraman; Christian Wolf
Journal:  Angew Chem Int Ed Engl       Date:  2016-12-27       Impact factor: 15.336

3.  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

4.  Modular synthesis of α-arylated carboxylic acids, esters and amides via photocatalyzed triple C-F bond cleavage of methyltrifluorides.

Authors:  Sifan Li; Paul W Davies; Wei Shu
Journal:  Chem Sci       Date:  2022-05-12       Impact factor: 9.969

5.  Chemodivergent Csp3─F bond functionalization and cross-electrophile alkyl-alkyl coupling with alkyl fluorides.

Authors:  Kaluvu Balaraman; Christian Wolf
Journal:  Sci Adv       Date:  2022-05-27       Impact factor: 14.957

6.  Silylated cyclopentadienes as competent silicon Lewis acid catalysts.

Authors:  M Alex Radtke; Tristan H Lambert
Journal:  Chem Sci       Date:  2018-06-29       Impact factor: 9.825

7.  Selective single C-F bond arylation of trifluoromethylalkene derivatives.

Authors:  Luning Tang; Ze-Yao Liu; Wenzhi She; Chao Feng
Journal:  Chem Sci       Date:  2019-08-05       Impact factor: 9.825

8.  Photocatalytic defluoroalkylation and hydrodefluorination of trifluoromethyls using o-phosphinophenolate.

Authors:  Can Liu; Ni Shen; Rui Shang
Journal:  Nat Commun       Date:  2022-01-17       Impact factor: 14.919

9.  Mechanochemical Conversion of Aromatic Amines to Aryl Trifluoromethyl Ethers.

Authors:  Michał Jakubczyk; Satenik Mkrtchyan; Mohanad Shkoor; Suneel Lanka; Šimon Budzák; Miroslav Iliaš; Marek Skoršepa; Viktor O Iaroshenko
Journal:  J Am Chem Soc       Date:  2022-06-02       Impact factor: 16.383

10.  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
  10 in total

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