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Literature DB >> 24162741

Trifluoromethyl ketones: properties, preparation, and application.

Christopher B Kelly¹, Michael A Mercadante, Nicholas E Leadbeater.

Abstract

Trifluoromethyl ketones (TFMKs) are exceedingly valuable synthetic targets in their own right and as synthons in the construction of fluorinated pharmacons. This Feature Article provides an overview of the properties of TFMKs, an in-depth discussion of the methods available for their synthesis, and two illustrative examples of their application as key intermediates in medicinal chemistry.

Entities: Chemical

Mesh：

Substances：

Year: 2013 PMID： 24162741 DOI： 10.1039/c3cc46266h

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

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Cited

7 in total

1. Nucleophilic Addition of Benzylboronates to Activated Ketones.

Authors: Jacob C Hayes; Michael R Hollerbach; Timothy J Barker
Journal: Tetrahedron Lett Date: 2019-12-16 Impact factor: 2.415

2. Synthesis and evaluation of phenylalanine-derived trifluoromethyl ketones for peptide-based oxidation catalysis.

Authors: Aaron L Featherston; Scott J Miller
Journal: Bioorg Med Chem Date: 2016-07-11 Impact factor: 3.641

3. Transition-Metal-Free Formation of C-E Bonds (E = C, N, O, S) and Formation of C-M Bonds (M = Mn, Mo) from N-Heterocyclic Carbene Mediated Fluoroalkene C-F Bond Activation.

Authors: Matthew C Leclerc; Bulat M Gabidullin; Jason G Da Gama; Stephanie L Daifuku; Theresa E Iannuzzi; Michael L Neidig; R Tom Baker
Journal: Organometallics Date: 2017-02-06 Impact factor: 3.876

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

Trifluoromethyl ketones: properties, preparation, and application.

1. Nucleophilic Addition of Benzylboronates to Activated Ketones.

2. Synthesis and evaluation of phenylalanine-derived trifluoromethyl ketones for peptide-based oxidation catalysis.

3. Transition-Metal-Free Formation of C-E Bonds (E = C, N, O, S) and Formation of C-M Bonds (M = Mn, Mo) from N-Heterocyclic Carbene Mediated Fluoroalkene C-F Bond Activation.

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

5. Radical Addition of Dihydroquinoxalin-2-ones to Trifluoromethyl Ketones under Visible-Light Photoredox Catalysis.

6. Direct Addition of Grignard Reagents to Aliphatic Carboxylic Acids Enabled by Bulky turbo-Organomagnesium Anilides.

7. Trisubstituted 2-trifluoromethyl pyrrolidines via catalytic asymmetric Michael addition/reductive cyclization.