Literature DB >> 24668827

Metal-free photochemical aromatic perfluoroalkylation of α-cyano arylacetates.

Manuel Nappi1, Giulia Bergonzini, Paolo Melchiorre.   

Abstract

We report here an operationally simple protocol for the direct aromatic perfluoroalkylation and trifluoromethylation of α-cyano arylacetates. This metal-free approach, which occurs at ambient temperature and under visible-light irradiation, is driven by the photochemical activity of electron donor-acceptor (EDA) complexes, formed in situ by the interaction of transiently generated enolates and perfluoroalkyl iodides. Preliminary mechanistic studies are reported.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CH functionalization; perfluoroalkylation; photochemistry; synthetic methods; trifluoromethylation

Year:  2014        PMID： 24668827     DOI： 10.1002/anie.201402008

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


  13 in total

Review 1.  Synthesis of Tri- and Difluoromethoxylated Compounds by Visible-Light Photoredox Catalysis.

Authors:  Johnny W Lee; Katarzyna N Lee; Ming-Yu Ngai
Journal:  Angew Chem Int Ed Engl       Date:  2019-05-28       Impact factor: 15.336

2.  Detection of Fleeting Amine Radical Cations and Elucidation of Chain Processes in Visible-Light-Mediated [3 + 2] Annulation by Online Mass Spectrometric Techniques.

Authors:  Yi Cai; Jiang Wang; Yuexiang Zhang; Zhi Li; David Hu; Nan Zheng; Hao Chen
Journal:  J Am Chem Soc       Date:  2017-08-25       Impact factor: 15.419

3.  Photochemical Perfluoroalkylation with Pyridine N-Oxides: Mechanistic Insights and Performance on a Kilogram Scale.

Authors:  Joel W Beatty; James J Douglas; Richard Miller; Rory C McAtee; Kevin P Cole; Corey R J Stephenson
Journal:  Chem       Date:  2016-09-08       Impact factor: 22.804

4.  Photochemical C-H acetalization of O-heterocycles utilizing phenylglyoxylic acid as the photoinitiator.

Authors:  Giorgos S Koutoulogenis; Nikoleta Spiliopoulou; Christoforos G Kokotos
Journal:  Photochem Photobiol Sci       Date:  2021-11-09       Impact factor: 4.328

5.  Photo-organocatalytic Enantioselective Perfluoroalkylation of β-Ketoesters.

Authors:  Łukasz Woźniak; John J Murphy; Paolo Melchiorre
Journal:  J Am Chem Soc       Date:  2015-04-24       Impact factor: 15.419

6.  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

7.  Catalyst-Free Deaminative Functionalizations of Primary Amines by Photoinduced Single-Electron Transfer.

Authors:  Jingjing Wu; Phillip S Grant; Xiabing Li; Adam Noble; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2019-03-14       Impact factor: 15.336

8.  Visible-Light-Mediated Generation of Nitrogen-Centered Radicals: Metal-Free Hydroimination and Iminohydroxylation Cyclization Reactions.

Authors:  Jacob Davies; Samuel G Booth; Stephanie Essafi; Robert A W Dryfe; Daniele Leonori
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-28       Impact factor: 15.336

9.  Selective C-O bond formation via a photocatalytic radical coupling strategy: access to perfluoroalkoxylated (ORF) arenes and heteroarenes.

Authors:  Johnny W Lee; Dominique N Spiegowski; Ming-Yu Ngai
Journal:  Chem Sci       Date:  2017-06-05       Impact factor: 9.825

10.  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
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