Literature DB >> 24038994

The critical effect of the countercation in the direct cupration of fluoroform with [Cu(OR)2 ](-).

Andrey I Konovalov1, Jordi Benet-Buchholz, Eddy Martin, Vladimir V Grushin.   

Abstract

Just a spectator or a key player? The alkali-metal counterion (K(+) ) plays a remarkable key role in the recently discovered cupration reaction of fluoroform with dialkoxycuprates. A total of eight Lewis acid and Lewis base centers synergistically interacting with one another arrange in a stable transition state, providing a low-energy pathway for this unique transformation.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CH activation; copper; fluorine; fluoroform; trifluoromethylation

Year:  2013        PMID： 24038994     DOI： 10.1002/anie.201306272

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


  5 in total

1.  Mechanism-based enhancement of scope and enantioselectivity for reactions involving a copper-substituted stereogenic carbon centre.

Authors:  Jaehee Lee; Suttipol Radomkit; Sebastian Torker; Juan Del Pozo; Amir H Hoveyda
Journal:  Nat Chem       Date:  2017-10-02       Impact factor: 24.427

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.  Catalytic Lewis Base Additive Enables Selective Copper-Catalyzed Borylative α-C-H Allylation of Alicyclic Amines.

Authors:  Borja Pérez-Saavedra; Álvaro Velasco-Rubio; Eva Rivera-Chao; Jesús A Varela; Carlos Saá; Martín Fañanás-Mastral
Journal:  J Am Chem Soc       Date:  2022-08-24       Impact factor: 16.383
  5 in total

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