Literature DB >> 29072350

Transition-Metal-Free Catalytic Hydrodefluorination of Polyfluoroarenes by Concerted Nucleophilic Aromatic Substitution with a Hydrosilicate.

Kotaro Kikushima1,2, Mary Grellier3,4, Masato Ohashi1, Sensuke Ogoshi1.   

Abstract

A transition-metal-free catalytic hydrodefluorination (HDF) reaction of polyfluoroarenes is described. The reaction involves direct hydride transfer from a hydrosilicate as the key intermediate, which is generated from a hydrosilane and a fluoride salt. The eliminated fluoride regenerates the hydrosilicate to complete the catalytic cycle. Dispersion-corrected DFT calculations indicated that the HDF reaction proceeds through a concerted nucleophilic aromatic substitution (CSN Ar) process.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  defluorination; fluoroarenes; hydride transfer; nucleophilic aromatic substitution; silicates

Year:  2017        PMID： 29072350     DOI： 10.1002/anie.201708003

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


  8 in total

Review 1.  Concerted Nucleophilic Aromatic Substitution Reactions.

Authors:  Simon Rohrbach; Andrew J Smith; Jia Hao Pang; Darren L Poole; Tell Tuttle; Shunsuke Chiba; John A Murphy
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-13       Impact factor: 15.336

2.  Catalyst-Free Hydrodefluorination of Perfluoroarenes with NaBH4.

Authors:  Timothy D Schoch; Mukulesh Mondal; Jimmie D Weaver
Journal:  Org Lett       Date:  2021-02-15       Impact factor: 6.005

3.  Development of a Fluorescent Nanofibrous Template by In Situ SNAr Polymerization of Fluorine-Containing Terphenyls with Aliphatic Diols: Self-Assembly and Optical and Liquid Crystal Properties.

Authors:  Sara A Alqarni; Salhah D Al-Qahtani; Ahmad A Alluhaybi; Rua B Alnoman; Amerah Alsoliemy; Shams H Abdel-Hafez; Nashwa M El-Metwaly
Journal:  ACS Omega       Date:  2021-12-08

4.  Synthesis and Characterization of Hypercoordinated Silicon Anions: Catching Intermediates of Lewis Base Catalysis.

Authors:  Nils Ansmann; Deborah Hartmann; Sonja Sailer; Philipp Erdmann; Rezisha Maskey; Marcel Schorpp; Lutz Greb
Journal:  Angew Chem Int Ed Engl       Date:  2022-05-05       Impact factor: 16.823

5.  Concerted nucleophilic aromatic substitutions.

Authors:  Eugene E Kwan; Yuwen Zeng; Harrison A Besser; Eric N Jacobsen
Journal:  Nat Chem       Date:  2018-07-16       Impact factor: 24.427

6.  Nucleophilic Aromatic Substitution of Polyfluoroarene to Access Highly Functionalized 10-Phenylphenothiazine Derivatives.

Authors:  Kotaro Kikushima; Haruka Koyama; Kazuki Kodama; Toshifumi Dohi
Journal:  Molecules       Date:  2021-03-04       Impact factor: 4.411

7.  Formation and Reactivity of a Hexahydridosilicate [SiH6 ]2- Coordinated by a Macrocycle-Supported Strontium Cation.

Authors:  Thomas Höllerhage; Priyabrata Ghana; Thomas P Spaniol; Ambre Carpentier; Laurent Maron; Ulli Englert; Jun Okuda
Journal:  Angew Chem Int Ed Engl       Date:  2022-01-14       Impact factor: 16.823

8.  Catalytic Hydrodefluorination via Oxidative Addition, Ligand Metathesis, and Reductive Elimination at Bi(I)/Bi(III) Centers.

Authors:  Yue Pang; Markus Leutzsch; Nils Nöthling; Felix Katzenburg; Josep Cornella
Journal:  J Am Chem Soc       Date:  2021-08-06       Impact factor: 15.419
  8 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.