Literature DB >> 27862770

Practical Photocatalytic Trifluoromethylation and Hydrotrifluoromethylation of Styrenes in Batch and Flow.

Natan J W Straathof1, Sten E Cramer1, Volker Hessel1, Timothy Noël1.   

Abstract

Styrenes represent a challenging class of substrates for current radical trifluoromethylation and hydrotrifluoromethylation methods due to a myriad of potential side reactions. Herein, we describe the development of mild, selective and broadly applicable photocatalytic trifluoromethylation and hydrotrifluoromethylation protocols for these challenging substrates. The methods use fac-Ir(ppy)3 , visible light and inexpensive CF3 I and can be applied to a diverse set of vinylarene substrates. The use of continuous-flow photochemical reaction conditions allowed to reduce the reaction time and increase the reaction selectivity.
© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  continuous flow; hydrotrifluoromethylation; microreactor; photoredox catalysis; trifluoromethylation

Year:  2016        PMID: 27862770     DOI: 10.1002/anie.201608297

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


  16 in total

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Review 3.  Recent advances in direct trifluoromethylation of olefinic C-H bonds.

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4.  Unsymmetrical difunctionalization of cyclooctadiene under continuous flow conditions: expanding the scope of ring opening metathesis polymerization.

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6.  Photocatalytic trifluoromethoxylation of arenes and heteroarenes in continuous-flow.

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7.  Practical and Regioselective Synthesis of C-4-Alkylated Pyridines.

Authors:  Jin Choi; Gabriele Laudadio; Edouard Godineau; Phil S Baran
Journal:  J Am Chem Soc       Date:  2021-07-28       Impact factor: 16.383

8.  Regio- and Stereoselective Radical Perfluoroalkyltriflation of Alkynes Using Phenyl(perfluoroalkyl)iodonium Triflates.

Authors:  Xi Wang; Armido Studer
Journal:  Org Lett       Date:  2017-05-18       Impact factor: 6.005

9.  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

10.  Markovnikov-Type Hydrotrifluoromethylchalcogenation of Unactivated Terminal Alkenes with [Me4N][XCF3] (X = S, Se) and TfOH.

Authors:  Jin Shi; Cheng-Pan Zhang
Journal:  Molecules       Date:  2020-10-03       Impact factor: 4.411

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