Literature DB >> 26499207

The Trifluoromethyl Anion.

Anton Lishchynskyi1, Fedor M Miloserdov1, Eddy Martin1, Jordi Benet-Buchholz1, Eduardo C Escudero-Adán1, Andrey I Konovalov1, Vladimir V Grushin2.   

Abstract

First evidence for the existence of free trifluoromethyl anion CF3 (-) has been obtained. The 3D-caged potassium cation in [K(crypt-222)](+) is inaccessible to CF3 (-) , thus rendering it uncoordinated ("naked"). Ionic [K(crypt-222)](+) CF3 (-) has been characterized by single-crystal X-ray diffraction, solution NMR spectroscopy, DFT calculations, and reactivity toward electrophiles.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  NMR spectroscopy; X-ray diffraction; carbanions; trifluoromethyl anion; trifluoromethylation

Year:  2015        PMID： 26499207     DOI： 10.1002/anie.201507356

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


  5 in total

Review 1.  Repurposing of F-gases: challenges and opportunities in fluorine chemistry.

Authors:  Daniel J Sheldon; Mark R Crimmin
Journal:  Chem Soc Rev       Date:  2022-06-20       Impact factor: 60.615

2.  Direct nucleophilic trifluoromethylation of carbonyl compounds by potent greenhouse gas, fluoroform: Improving the reactivity of anionoid trifluoromethyl species in glymes.

Authors:  Takuya Saito; Jiandong Wang; Etsuko Tokunaga; Seiji Tsuzuki; Norio Shibata
Journal:  Sci Rep       Date:  2018-07-31       Impact factor: 4.379

3.  Gas/Liquid-Phase Micro-Flow Trifluoromethylation using Fluoroform: Trifluoromethylation of Aldehydes, Ketones, Chalcones, and N-Sulfinylimines.

Authors:  Kazuki Hirano; Satoshi Gondo; Nagender Punna; Etsuko Tokunaga; Norio Shibata
Journal:  ChemistryOpen       Date:  2019-02-05       Impact factor: 2.911

4.  Synthesis of trifluoromethyl ketones by nucleophilic trifluoromethylation of esters under a fluoroform/KHMDS/triglyme system.

Authors:  Yamato Fujihira; Yumeng Liang; Makoto Ono; Kazuki Hirano; Takumi Kagawa; Norio Shibata
Journal:  Beilstein J Org Chem       Date:  2021-02-12       Impact factor: 2.883

5.  In Situ Studies of Arylboronic Acids/Esters and R3SiCF3 Reagents: Kinetics, Speciation, and Dysfunction at the Carbanion-Ate Interface.

Authors:  Andrés García-Domínguez; Andrew G Leach; Guy C Lloyd-Jones
Journal:  Acc Chem Res       Date:  2022-04-18       Impact factor: 24.466
  5 in total

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