Literature DB >> 27872511

Synthesis of Trifluoromethoxylated (Hetero)Arenes via OCF3 Migration.

Katarzyna N Lee1, Johnny W Lee1, Ming-Yu Ngai1.   

Abstract

Incorporation of the OCF3 group into organic molecules, especially aromatic and heteroaromatic compounds, is recognized as one of the major challenges in synthetic organic chemistry. Although many attempts have been made to develop efficient trifluoromethoxylation strategies, most of the current approaches still require use of highly toxic, thermally unstable reagents, or impractical reaction conditions. Herein, we highlight a recent contribution from our group towards the synthesis of (hetero)aryltrifluoromethyl ethers. Our protocol is scalable, operationally simple, and allows an easy access to a wide range of synthetically useful ortho-OCF3 aniline derivatives, as well as functionalized trifluoromethoxylated pyridines and pyrimidines under mild reaction conditions.

Entities:  

Keywords:  amides; anilines; fluorine; rearrangement; trifluoromethoxylation; trifluoromethylation

Year:  2015        PMID: 27872511      PMCID: PMC5115881          DOI: 10.1055/s-0035-1560516

Source DB:  PubMed          Journal:  Synlett        ISSN: 0936-5214            Impact factor:   2.454


  24 in total

1.  CF3 oxonium salts, O-(trifluoromethyl)dibenzofuranium salts: in situ synthesis, properties, and application as a real CF3+ species reagent.

Authors:  Teruo Umemoto; Kenji Adachi; Sumi Ishihara
Journal:  J Org Chem       Date:  2007-08-04       Impact factor: 4.354

Review 2.  Alpha-fluorinated ethers, thioethers, and amines: anomerically biased species.

Authors:  Frédéric Leroux; Peter Jeschke; Manfred Schlosser
Journal:  Chem Rev       Date:  2005-03       Impact factor: 60.622

3.  Rearrangement of N-oxyenamines and related reactions.

Authors:  Andrey A Tabolin; Sema L Ioffe
Journal:  Chem Rev       Date:  2014-03-14       Impact factor: 60.622

Review 4.  Trifluoromethyl ethers and -thioethers as tools for medicinal chemistry and drug discovery.

Authors:  Gregory Landelle; Armen Panossian; Frederic R Leroux
Journal:  Curr Top Med Chem       Date:  2014       Impact factor: 3.295

5.  The trifluoromethoxy group: a long-range electron-withdrawing substituent.

Authors:  Eva Castagnetti; Manfred Schlosser
Journal:  Chemistry       Date:  2002-02-15       Impact factor: 5.236

Review 6.  Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001-2011).

Authors:  Jiang Wang; María Sánchez-Roselló; José Luis Aceña; Carlos del Pozo; Alexander E Sorochinsky; Santos Fustero; Vadim A Soloshonok; Hong Liu
Journal:  Chem Rev       Date:  2013-12-03       Impact factor: 60.622

7.  Celikalim (WAY-120491) increases K+ outward flux in dog and human airway smooth muscle.

Authors:  F G de Lorenzi
Journal:  Pulm Pharmacol       Date:  1994-04

Review 8.  Understanding organofluorine chemistry. An introduction to the C-F bond.

Authors:  David O'Hagan
Journal:  Chem Soc Rev       Date:  2007-10-17       Impact factor: 54.564

9.  Silver-Mediated Oxidative Trifluoromethylation of Phenols: Direct Synthesis of Aryl Trifluoromethyl Ethers.

Authors:  Jian-Bo Liu; Chao Chen; Lingling Chu; Zeng-Hao Chen; Xiu-Hua Xu; Feng-Ling Qing
Journal:  Angew Chem Int Ed Engl       Date:  2015-08-12       Impact factor: 15.336

10.  Trifluoromethyl ethers--synthesis and properties of an unusual substituent.

Authors:  Frédéric R Leroux; Baptiste Manteau; Jean-Pierre Vors; Sergiy Pazenok
Journal:  Beilstein J Org Chem       Date:  2008-04-29       Impact factor: 2.883

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  7 in total

1.  Redox-Active Reagents for Photocatalytic Generation of the OCF3 Radical and (Hetero)Aryl C-H Trifluoromethoxylation.

Authors:  Weijia Zheng; Johnny W Lee; Cristian A Morales-Rivera; Peng Liu; Ming-Yu Ngai
Journal:  Angew Chem Int Ed Engl       Date:  2018-09-20       Impact factor: 15.336

Review 2.  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

3.  Catalytic C-H Trifluoromethoxylation of Arenes and Heteroarenes.

Authors:  Weijia Zheng; Cristian A Morales-Rivera; Johnny W Lee; Peng Liu; Ming-Yu Ngai
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-13       Impact factor: 15.336

4.  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

5.  Mechanochemical Conversion of Aromatic Amines to Aryl Trifluoromethyl Ethers.

Authors:  Michał Jakubczyk; Satenik Mkrtchyan; Mohanad Shkoor; Suneel Lanka; Šimon Budzák; Miroslav Iliaš; Marek Skoršepa; Viktor O Iaroshenko
Journal:  J Am Chem Soc       Date:  2022-06-02       Impact factor: 16.383

6.  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

7.  Rapid Dehydroxytrifluoromethoxylation of Alcohols.

Authors:  Wei Zhang; Jia Chen; Jin-Hong Lin; Ji-Chang Xiao; Yu-Cheng Gu
Journal:  iScience       Date:  2018-07-11
  7 in total

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