Literature DB >> 30919544

Efficient Synthesis of α-Trifluoromethyl Carboxylic Acids and Esters through Fluorocarboxylation of gem-Difluoroalkenes.

Woo-Jin Yoo1, Junpei Kondo2, José A Rodríguez-Santamaría2, Thanh V Q Nguyen2, Shū Kobayashi1,2.   

Abstract

A facile synthetic procedure for the preparation of α-trifluoromethyl carboxylic acids and esters was achieved through multicomponent coupling reactions between gem-difluoroalkenes, cesium fluoride, and carbon dioxide. The products were generated in moderate to excellent yields, and the synthetic utility of this method was demonstrated through the preparation of trifluoromethylated versions of popular nonsteroidal anti-inflammatory drugs (NSAIDs).
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  carbon dioxide; carboxylic acids; cesium fluoride; fluorination; gem-difluoroalkenes

Year:  2019        PMID： 30919544     DOI： 10.1002/anie.201902779

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


  5 in total

1.  Catalyzing the Hydrodefluorination of CF3-Substituted Alkenes by PhSiH3. H• Transfer from a Nickel Hydride.

Authors:  Chengbo Yao; Shuai Wang; Jack Norton; Matthew Hammond
Journal:  J Am Chem Soc       Date:  2020-01-24       Impact factor: 15.419

2.  Cu(II)-Catalyzed Unsymmetrical Dioxidation of gem-Difluoroalkenes to Generate α,α-Difluorinated-α-phenoxyketones.

Authors:  Suvajit Koley; Kaylee T Cayton; Gisela A González-Montiel; M Ramu Yadav; Douglas L Orsi; Andrew J Intelli; Paul Ha-Yeon Cheong; Ryan A Altman
Journal:  J Org Chem       Date:  2022-08-01       Impact factor: 4.198

3.  Photocarboxylation of Benzylic C-H Bonds.

Authors:  Qing-Yuan Meng; Tobias E Schirmer; Anna Lucia Berger; Karsten Donabauer; Burkhard König
Journal:  J Am Chem Soc       Date:  2019-07-11       Impact factor: 15.419

4.  Synthesis of bioactive fluoropyrrolidines via copper(i)-catalysed asymmetric 1,3-dipolar cycloaddition of azomethine ylides.

Authors:  Xiao Xu; Longzhu Bao; Lu Ran; Zhenyan Yang; Dingce Yan; Chun-Jiang Wang; Huailong Teng
Journal:  Chem Sci       Date:  2021-12-07       Impact factor: 9.825

5.  Umpolung Difunctionalization of Carbonyls via Visible-Light Photoredox Catalytic Radical-Carbanion Relay.

Authors:  Shun Wang; Bei-Yi Cheng; Matea Sršen; Burkhard König
Journal:  J Am Chem Soc       Date:  2020-04-13       Impact factor: 15.419
  5 in total

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