Literature DB >> 29927506

Radical Trifluoromethoxylation of Arenes Triggered by a Visible-Light-Mediated N-O Bond Redox Fragmentation.

Benson J Jelier1, Pascal F Tripet1, Ewa Pietrasiak1, Ivan Franzoni2, Gunnar Jeschke1, Antonio Togni1.   

Abstract

A simple trifluoromethoxylation method enables non-directed functionalization of C-H bonds on a range of substrates, providing access to aryl trifluoromethyl ethers. This light-driven process is distinctly different from conventional procedures and occurs through an OCF3 radical mechanism mediated by a photoredox catalyst, which triggers an N-O bond fragmentation. The pyridinium-based trifluoromethoxylation reagent is bench-stable and provides access to synthetic diversity in lead compounds in an operationally simple manner.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  late-stage functionalization; organofluorine compounds; photoredox; radical mechanisms; trifluoromethoxylation

Year:  2018        PMID: 29927506     DOI: 10.1002/anie.201806296

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


  11 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.  Redox-Neutral TEMPO Catalysis: Direct Radical (Hetero)Aryl C-H Di- and Trifluoromethoxylation.

Authors:  Johnny W Lee; Sanghyun Lim; Daniel N Maienshein; Peng Liu; Ming-Yu Ngai
Journal:  Angew Chem Int Ed Engl       Date:  2020-09-24       Impact factor: 15.336

3.  Diversification of Amidyl Radical Intermediates Derived from C-H Aminopyridylation.

Authors:  Asim Maity; Pritam Roychowdhury; Roberto G Herrera; David C Powers
Journal:  Org Lett       Date:  2022-04-04       Impact factor: 6.072

4.  Trifluoromethyl Nonaflate: A Practical Trifluoromethoxylating Reagent and its Application to the Regio- and Stereoselective Synthesis of Trifluoromethoxylated Alkenes.

Authors:  Zhichao Lu; Tatsuya Kumon; Gerald B Hammond; Teruo Umemoto
Journal:  Angew Chem Int Ed Engl       Date:  2021-06-17       Impact factor: 16.823

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

Authors:  Alexander V Nyuchev; Ting Wan; Borja Cendón; Carlo Sambiagio; Job J C Struijs; Michelle Ho; Moisés Gulías; Ying Wang; Timothy Noël
Journal:  Beilstein J Org Chem       Date:  2020-06-15       Impact factor: 2.883

Review 6.  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

7.  Accelerating fragment-based library generation by coupling high-performance photoreactors with benchtop analysis.

Authors:  Quentin Lefebvre; Christophe Salomé; Thomas C Fessard
Journal:  Beilstein J Org Chem       Date:  2020-05-12       Impact factor: 2.883

8.  Manganese-Catalyzed Electrochemical Deconstructive Chlorination of Cycloalkanols via Alkoxy Radicals.

Authors:  Benjamin D W Allen; Mishra Deepak Hareram; Alex C Seastram; Tom McBride; Thomas Wirth; Duncan L Browne; Louis C Morrill
Journal:  Org Lett       Date:  2019-11-05       Impact factor: 6.005

9.  Nucleophilic trifluoromethoxylation of alkyl halides without silver.

Authors:  Yan Li; Yang Yang; Jinrui Xin; Pingping Tang
Journal:  Nat Commun       Date:  2020-02-06       Impact factor: 14.919

Review 10.  Late stage C-H functionalization via chalcogen and pnictogen salts.

Authors:  Christopher B Kelly; Rosaura Padilla-Salinas
Journal:  Chem Sci       Date:  2020-09-07       Impact factor: 9.825

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