Literature DB >> 26840376

Visible Light-Promoted Decarboxylative Di- and Trifluoromethylthiolation of Alkyl Carboxylic Acids.

Lisa Candish1, Lena Pitzer1, Adrián Gómez-Suárez1, Frank Glorius2.   

Abstract

Described herein is a new and straightforward decarboxylative di- and trifluoromethylthiolation of alkyl carboxylic acids promoted by visible light. This approach enables the synthesis of biologically relevant alkyl SCF2H and SCF3 compounds from cheap and abundant carboxylic acids. The method is operationally simple, using irradiation from household light sources, and its mild reaction conditions make it tolerant of a range of functional groups. The strategy employs electrophilic phthalimide-derived di- and trifluoromethylthiolation reagents and exploits the ability of the imidyl radical to carry a radical chain.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  decarboxylation; difluoromethylthiolation; photocatalysis; trifluoromethylthiolation; visible light

Year:  2016        PMID: 26840376     DOI: 10.1002/chem.201600421

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  8 in total

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Authors:  Laura Buglioni; Fabian Raymenants; Aidan Slattery; Stefan D A Zondag; Timothy Noël
Journal:  Chem Rev       Date:  2021-08-10       Impact factor: 60.622

2.  Catalyst-Free Decarbonylative Trifluoromethylthiolation Enabled by Electron Donor-Acceptor Complex Photoactivation.

Authors:  Alexander Lipp; Shorouk O Badir; Ryan Dykstra; Osvaldo Gutierrez; Gary A Molander
Journal:  Adv Synth Catal       Date:  2021-05-19       Impact factor: 5.981

3.  Mild, visible light-mediated decarboxylation of aryl carboxylic acids to access aryl radicals.

Authors:  L Candish; M Freitag; T Gensch; F Glorius
Journal:  Chem Sci       Date:  2017-02-27       Impact factor: 9.825

Review 4.  Recent advances in transition-metal-catalyzed incorporation of fluorine-containing groups.

Authors:  Xiaowei Li; Xiaolin Shi; Xiangqian Li; Dayong Shi
Journal:  Beilstein J Org Chem       Date:  2019-09-23       Impact factor: 2.883

5.  A Pd-Catalyzed [4 + 2] Annulation Approach to Fluorinated N-Heterocycles.

Authors:  Víctor García-Vázquez; Larry Hoteite; Christopher P Lakeland; David W Watson; Joseph P A Harrity
Journal:  Org Lett       Date:  2021-03-24       Impact factor: 6.005

6.  Blue light photoredox-catalysed acetalation of alkynyl bromides.

Authors:  Xue-Li Lyu; Shi-Sheng Huang; Hong-Jian Song; Yu-Xiu Liu; Qing-Min Wang
Journal:  RSC Adv       Date:  2019-11-06       Impact factor: 4.036

7.  Generation of Alkyl Radicals: From the Tyranny of Tin to the Photon Democracy.

Authors:  Stefano Crespi; Maurizio Fagnoni
Journal:  Chem Rev       Date:  2020-08-06       Impact factor: 60.622

8.  Phenylene-bridged bis(benzimidazolium) (BBIm2+): a dicationic organic photoredox catalyst.

Authors:  Takuya Kodama; Maiko Kubo; Wataru Shinji; Kei Ohkubo; Mamoru Tobisu
Journal:  Chem Sci       Date:  2020-10-07       Impact factor: 9.825

  8 in total

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