Literature DB >> 29023131

Direct Synthesis of Acyl Fluorides from Carboxylic Acids with the Bench-Stable Solid Reagent (Me4N)SCF3.

Thomas Scattolin1, Kristina Deckers1, Franziska Schoenebeck1.   

Abstract

A convenient, highly efficient, and selective transformation of aliphatic and aromatic carboxylic acids to acyl fluorides is reported. In contrast to established approaches that require toxic or volatile additives and base and reaction control (i.e., cooling, slow addition), this protocol allows for a straightforward access to various R-COF entities upon direct reaction with the bench-stable, solid reagent (Me4N)SCF3 at room temperature. The method is base- and additive-free, compatible with late-stage synthetic applications, high functional group tolerance, and facile target compound purification via filtration.

Entities:  

Year:  2017        PMID: 29023131     DOI: 10.1021/acs.orglett.7b02516

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  6 in total

1.  N-Hydroxybenzimidazole as a structurally modifiable platform for N-oxyl radicals for direct C-H functionalization reactions.

Authors:  Tomomi Yoshii; Saori Tsuzuki; Shunya Sakurai; Ryu Sakamoto; Julong Jiang; Miho Hatanaka; Akira Matsumoto; Keiji Maruoka
Journal:  Chem Sci       Date:  2020-05-18       Impact factor: 9.825

2.  Nucleophilic Fluorination Catalyzed by a Cyclometallated Rhodium Complex.

Authors:  Patrick J Morgan; Graham C Saunders; Stuart A Macgregor; Andrew C Marr; Peter Licence
Journal:  Organometallics       Date:  2022-03-31       Impact factor: 3.837

3.  Deoxyfluorination of acyl fluorides to trifluoromethyl compounds by FLUOLEAD®/Olah's reagent under solvent-free conditions.

Authors:  Yumeng Liang; Akihito Taya; Zhengyu Zhao; Norimichi Saito; Norio Shibata
Journal:  Beilstein J Org Chem       Date:  2020-12-14       Impact factor: 2.883

4.  Electrophilic Reagents for the Direct Incorporation of Uncommon SCF2CF2H and SCF2CF3 Motifs.

Authors:  Jordi Mestre; Miguel Bernús; Sergio Castillón; Omar Boutureira
Journal:  J Org Chem       Date:  2022-08-09       Impact factor: 4.198

5.  Palladium-Catalyzed Decarbonylative Trifluoromethylation of Acid Fluorides.

Authors:  Sinead T Keaveney; Franziska Schoenebeck
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-13       Impact factor: 15.336

6.  Deoxygenative trifluoromethylthiolation of carboxylic acids.

Authors:  Runze Mao; Srikrishna Bera; Alexis Cheseaux; Xile Hu
Journal:  Chem Sci       Date:  2019-08-26       Impact factor: 9.825

  6 in total

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