Literature DB >> 22998369

Trifluoromethylation of α-haloketones.

Petr Novák1, Anton Lishchynskyi, Vladimir V Grushin.   

Abstract

The C-X bond (X = Br, Cl) of α-haloketones is smoothly trifluoromethylated with the fluoroform-derived CuCF(3) reagent recently developed in our laboratories. This is the first nucleophilic α-trifluoromethylation reaction of carbonyl compounds and a rare example of CF(3)-C(sp(3)) coupling. The transformation employs only low-cost chemicals and cleanly occurs in up to 99% yield at room temperature, thereby providing an unprecedentedly easy entry to valuable 2,2,2-trifluoroethylketones.

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Year:  2012        PMID: 22998369     DOI: 10.1021/ja307783w

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  7 in total

1.  Synthesis of 1,2-Bis(trifluoromethylthio)arenes via Aryne Intermediates.

Authors:  Milad Mesgar; Olafs Daugulis
Journal:  Org Lett       Date:  2017-07-28       Impact factor: 6.005

Review 2.  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

3.  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

4.  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

5.  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

Review 6.  3-(Bromoacetyl)coumarins: unraveling their synthesis, chemistry, and applications.

Authors:  Moaz M Abdou; Ahmed Abu-Rayyan; Ahmed G Bedir; S Abdel-Fattah; A M A Omar; Abdullah A Ahmed; El-Sayed I El-Desoky; Eslam A Ghaith
Journal:  RSC Adv       Date:  2021-11-29       Impact factor: 3.361

7.  Organocatalyzed Trifluoromethylation of Ketones and Sulfonyl Fluorides by Fluoroform under a Superbase System.

Authors:  Satoshi Okusu; Kazuki Hirano; Etsuko Tokunaga; Norio Shibata
Journal:  ChemistryOpen       Date:  2015-08-06       Impact factor: 2.911

  7 in total

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