Literature DB >> 25295971

Chemo-, regio-, and stereoselective trifluoromethylation of styrenes via visible light-driven single-electron transfer (SET) and triplet-triplet energy transfer (TTET) processes.

Qing-Yu Lin1, Xiu-Hua Xu, Feng-Ling Qing.   

Abstract

A process for tunable and chemo-, regio-, and stereoselective photocatalytic trifluoromethylation of styrenes was developed. Thermodynamically stable E-trifluoromethylated alkenes were prepared using Togni's reagent in the presence of Ru(bpy)3Cl2·6H2O under visible light irradiation, whereas less thermodynamically stable Z-trifluoromethylated alkenes were obtained by employing Umemoto's reagent and photocatalyst Ir(ppy)3.

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Year:  2014        PMID： 25295971     DOI： 10.1021/jo502040t

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  12 in total

1.  Molybdenum chloride catalysts for Z-selective olefin metathesis reactions.

Authors:  Ming Joo Koh; Thach T Nguyen; Jonathan K Lam; Sebastian Torker; Jakub Hyvl; Richard R Schrock; Amir H Hoveyda
Journal:  Nature       Date:  2017-01-23       Impact factor: 49.962

2.  Photocatalytic C-F Reduction and Functionalization.

Authors:  Sameera Senaweera; Jimmie D Weaver
Journal:  Aldrichimica Acta       Date:  2016       Impact factor: 3.667

3.  Catalyst-Free Hydrodefluorination of Perfluoroarenes with NaBH4.

Authors:  Timothy D Schoch; Mukulesh Mondal; Jimmie D Weaver
Journal:  Org Lett       Date:  2021-02-15       Impact factor: 6.005

Review 4.  Recent advances in direct trifluoromethylation of olefinic C-H bonds.

Authors:  Cao Yang; Akbar Hassanpour; Khatereh Ghorbanpour; Shahrzad Abdolmohammadi; Esmail Vessally
Journal:  RSC Adv       Date:  2019-09-03       Impact factor: 4.036

5.  Product Control in Alkene Trifluoromethylation: Hydrotrifluoromethylation, Vinylic Trifluoromethylation, and Iodotrifluoromethylation using Togni Reagent.

Authors:  Hiromichi Egami; Yoshihiko Usui; Shintaro Kawamura; Sayoko Nagashima; Mikiko Sodeoka
Journal:  Chem Asian J       Date:  2015-06-16

6.  Photocatalyst size controls electron and energy transfer: selectable E/Z isomer synthesis via C-F alkenylation.

Authors:  A Singh; C J Fennell; J D Weaver
Journal:  Chem Sci       Date:  2016-07-21       Impact factor: 9.825

7.  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

8.  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

9.  Ruthenium-Catalyzed Site-Selective Trifluoromethylations and (Per)Fluoroalkylations of Anilines and Indoles.

Authors:  Yang Li; Helfried Neumann; Matthias Beller
Journal:  Chemistry       Date:  2020-05-12       Impact factor: 5.236

Review 10.  Photosensitized direct C-H fluorination and trifluoromethylation in organic synthesis.

Authors:  Shahboz Yakubov; Joshua P Barham
Journal:  Beilstein J Org Chem       Date:  2020-09-03       Impact factor: 2.883
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