Literature DB >> 26880666

Visible-Light-Promoted Trifluoromethylthiolation of Styrenes by Dual Photoredox/Halide Catalysis.

Roman Honeker1, R Aleyda Garza-Sanchez1, Matthew N Hopkinson2, Frank Glorius3.   

Abstract

Herein, we report a new visible-light-promoted strategy to access radical trifluoromethylthiolation reactions by combining halide and photoredox catalysis. This approach allows for the synthesis of vinyl-SCF3 compounds of relevance in pharmaceutical chemistry directly from alkenes under mild conditions with irradiation from household light sources. Furthermore, alkyl-SCF3-containing cyclic ketone and oxindole derivatives can be accessed by radical-polar crossover semi-pinacol and cyclization processes. Inexpensive halide salts play a crucial role in activating the trifluoromethylthiolating reagent towards photoredox catalysis and aid the formation of the SCF3 radical.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  halides; photocatalysis; synthetic methods; trifluoromethylthiolation; visible light

Mesh:

Substances:

Year:  2016        PMID: 26880666     DOI: 10.1002/chem.201600190

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


  6 in total

Review 1.  Dual Catalysis Strategies in Photochemical Synthesis.

Authors:  Kazimer L Skubi; Travis R Blum; Tehshik P Yoon
Journal:  Chem Rev       Date:  2016-04-25       Impact factor: 60.622

2.  Dual gold and photoredox catalysis: visible light-mediated intermolecular atom transfer thiosulfonylation of alkenes.

Authors:  Haoyu Li; Cuicui Shan; Chen-Ho Tung; Zhenghu Xu
Journal:  Chem Sci       Date:  2017-01-04       Impact factor: 9.825

Review 3.  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

4.  Cascade trifluoromethylthiolation and cyclization of N-[(3-aryl)propioloyl]indoles.

Authors:  Ming-Xi Bi; Shuai Liu; Yangen Huang; Xiu-Hua Xu; Feng-Ling Qing
Journal:  Beilstein J Org Chem       Date:  2020-04-08       Impact factor: 2.883

5.  Metal-free visible-light-enabled vicinal trifluoromethyl dithiolation of unactivated alkenes.

Authors:  Xiaojuan Li; Qiang Zhang; Weigang Zhang; Jinzhu Ma; Yi Wang; Yi Pan
Journal:  Beilstein J Org Chem       Date:  2021-02-24       Impact factor: 2.883

6.  Visible-Light Photocatalytic Decarboxylation of α,β-Unsaturated Carboxylic Acids: Facile Access to Stereoselective Difluoromethylated Styrenes in Batch and Flow.

Authors:  Xiao-Jing Wei; Wout Boon; Volker Hessel; Timothy Noël
Journal:  ACS Catal       Date:  2017-09-11       Impact factor: 13.084

  6 in total

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