Literature DB >> 30943329

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

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

Abstract

Trifluoromethoxy (OCF3 ) and difluoromethoxy (OCF2 H) groups are fluorinated structural motifs that exhibit unique physicochemical characteristics. Incorporation of these substituents into organic molecules is a highly desirable approach used in medicinal chemistry and drug discovery processes to alter the properties of a parent compound. Recently, tri- and difluoromethyl ethers have received increasing attention and several innovative strategies to access these valuable functional groups have been developed. The focus of this Minireview is the use of visible-light photoredox catalysis in the synthesis of tri- and difluoromethyl ethers. Recent photocatalytic strategies for the formation of O-CF3 , C-OCF3, O-CF2 H, and C-OCF2 H bonds as well as other transformations leading to the construction of ORF groups are discussed herein.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  drug discovery; fluorine; photochemistry; radicals; synthetic methods

Year:  2019        PMID: 30943329      PMCID: PMC7001783          DOI: 10.1002/anie.201902243

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


  47 in total

Review 1.  A "Renaissance" in radical trifluoromethylation.

Authors:  Armido Studer
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-13       Impact factor: 15.336

2.  A Radical Revolution for Trifluoromethoxylation.

Authors:  Basudev Sahoo; Matthew N Hopkinson
Journal:  Angew Chem Int Ed Engl       Date:  2018-06-11       Impact factor: 15.336

Review 3.  Synthetic Approaches to Trifluoromethoxy-Substituted Compounds.

Authors:  Anis Tlili; Fabien Toulgoat; Thierry Billard
Journal:  Angew Chem Int Ed Engl       Date:  2016-07-28       Impact factor: 15.336

4.  Fluorine in drug design: a case study with fluoroanisoles.

Authors:  Li Xing; David C Blakemore; Arjun Narayanan; Ray Unwalla; Frank Lovering; R Aldrin Denny; Huanyu Zhou; Mark E Bunnage
Journal:  ChemMedChem       Date:  2015-03-06       Impact factor: 3.466

Review 5.  Phosphodiesterase 4 inhibitors for chronic obstructive pulmonary disease.

Authors:  Jimmy Chong; Bonnie Leung; Phillippa Poole
Journal:  Cochrane Database Syst Rev       Date:  2017-09-19

6.  Trifluoromethoxylation of arenes: synthesis of ortho-trifluoromethoxylated aniline derivatives by OCF3 migration.

Authors:  Katarzyna N Hojczyk; Pengju Feng; Chengbo Zhan; Ming-Yu Ngai
Journal:  Angew Chem Int Ed Engl       Date:  2014-10-30       Impact factor: 15.336

7.  Recent Development of Catalytic Trifluoromethoxylation Reactions.

Authors:  Katarzyna N Lee; Johnny W Lee; Ming-Yu Ngai
Journal:  Tetrahedron       Date:  2018-09-13       Impact factor: 2.457

8.  Synthesis of gem-difluorocyclopropa(e)nes and O-, S-, N-, and P-difluoromethylated compounds with TMSCF(2)Br.

Authors:  Lingchun Li; Fei Wang; Chuanfa Ni; Jinbo Hu
Journal:  Angew Chem Int Ed Engl       Date:  2013-09-12       Impact factor: 15.336

9.  A scalable and operationally simple radical trifluoromethylation.

Authors:  Joel W Beatty; James J Douglas; Kevin P Cole; Corey R J Stephenson
Journal:  Nat Commun       Date:  2015-08-10       Impact factor: 14.919

10.  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

View more
  6 in total

1.  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

2.  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 3.  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

4.  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

5.  De novo design and synthesis of dipyridopurinone derivatives as visible-light photocatalysts in productive guanylation reactions.

Authors:  Yameng Wan; Hao Wu; Nana Ma; Jie Zhao; Zhiguo Zhang; Wenjing Gao; Guisheng Zhang
Journal:  Chem Sci       Date:  2021-11-13       Impact factor: 9.825

6.  Trifluoromethoxypyrazines: Preparation and Properties.

Authors:  Taras M Sokolenko; Yurii L Yagupolskii
Journal:  Molecules       Date:  2020-05-09       Impact factor: 4.411

  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.