Literature DB >> 25907421

Direct Aromatic C-H Trifluoromethylation via an Electron-Donor-Acceptor Complex.

Yuanzheng Cheng1, Xiangai Yuan2, Jing Ma3, Shouyun Yu4.   

Abstract

A novel electron-donor-acceptor (EDA) complex-mediated direct C-H trifluoromethylation of arenes with Umemoto's reagent has been developed. This transformation has been enabled by an unprecedented EDA complex formed by Umemoto's reagent and an amine, which was supported by experiments and theoretical calculations. The radical-based methodology presented here allows to access highly-functionalized trifluoromethyl arenes in up to 81 % chemical yield.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CH functionalization; arenes; donor-acceptor systems; electron transfer; trifluoromethylation

Year:  2015        PMID： 25907421     DOI： 10.1002/chem.201500896

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


  9 in total

1.  Trifluoromethylation of Secondary Nitroalkanes.

Authors:  Amber A S Gietter-Burch; Vijayarajan Devannah; Donald A Watson
Journal:  Org Lett       Date:  2017-05-23       Impact factor: 6.005

2.  Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.

Authors:  Daniel Kaiser; Immo Klose; Rik Oost; James Neuhaus; Nuno Maulide
Journal:  Chem Rev       Date:  2019-06-25       Impact factor: 60.622

3.  Enantiospecific Trifluoromethyl-Radical-Induced Three-Component Coupling of Boronic Esters with Furans.

Authors:  Yahui Wang; Adam Noble; Christopher Sandford; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2017-01-18       Impact factor: 15.336

4.  Enantioselective radical conjugate additions driven by a photoactive intramolecular iminium-ion-based EDA complex.

Authors:  Zhong-Yan Cao; Tamal Ghosh; Paolo Melchiorre
Journal:  Nat Commun       Date:  2018-08-16       Impact factor: 14.919

5.  Cu and Hydroquinone for the Trifluoromethylation of Unprotected Phenols.

Authors:  Jakob Pletz; Christoph Koeberl; Michael Fuchs; Oliver Steiner; Walter Goessler; Wolfgang Kroutil
Journal:  European J Org Chem       Date:  2018-10-08

6.  Visible-light Promoted Atom Transfer Radical Addition-Elimination (ATRE) Reaction for the Synthesis of Fluoroalkylated Alkenes Using DMA as Electron-Donor.

Authors:  Wen-Wen Xu; Le Wang; Ting Mao; Jiwei Gu; Xiao-Fei Li; Chun-Yang He
Journal:  Molecules       Date:  2020-01-24       Impact factor: 4.411

7.  Synthetic Methods Driven by the Photoactivity of Electron Donor-Acceptor Complexes.

Authors:  Giacomo E M Crisenza; Daniele Mazzarella; Paolo Melchiorre
Journal:  J Am Chem Soc       Date:  2020-03-12       Impact factor: 15.419

8.  An Efficient Approach to 2-CF3-Indoles Based on ortho-Nitrobenzaldehydes.

Authors:  Vasiliy M Muzalevskiy; Zoia A Sizova; Vladimir T Abaev; Valentine G Nenajdenko
Journal:  Molecules       Date:  2021-12-04       Impact factor: 4.411

9.  Synthesis of N-aryl amines enabled by photocatalytic dehydrogenation.

Authors:  Jungwon Kim; Siin Kim; Geunho Choi; Geun Seok Lee; Donghyeok Kim; Jungkweon Choi; Hyotcherl Ihee; Soon Hyeok Hong
Journal:  Chem Sci       Date:  2020-12-08       Impact factor: 9.825
  9 in total

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