Literature DB >> 31199418

Metal-free defluorinative arylation of trifluoromethyl alkenes via photoredox catalysis.

Rebecca J Wiles1, James P Phelan1, Gary A Molander1.   

Abstract

Literature methods to access gem-difluoroalkenes are largely limited to harsh, organometallic-based methods, and known photoredox-mediated processes are not amenable to aryl radical addition to trifluoromethyl alkenes. A metal-free, functional group-tolerant method for the preparation of benzylic gem-difluoroalkenes is described. Halogen atom abstraction from (hetero)aryl halides generates aryl radicals that undergo a defluorinative arylation of α-trifluoromethyl alkenes, tolerating electronically disparate aryl radicals and α-trifluoromethyl alkenes.

Entities:  

Year:  2019        PMID: 31199418      PMCID: PMC7210470          DOI: 10.1039/c9cc04265b

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  31 in total

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Authors:  Petra Malátková; Vladimír Wsól
Journal:  Drug Metab Rev       Date:  2013-10-31       Impact factor: 4.518

Review 3.  Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

Authors:  Christopher K Prier; Danica A Rankic; David W C MacMillan
Journal:  Chem Rev       Date:  2013-03-19       Impact factor: 60.622

4.  The unique fluorine effects in organic reactions: recent facts and insights into fluoroalkylations.

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Journal:  Chem Soc Rev       Date:  2016-08-08       Impact factor: 54.564

5.  Visible Light Mediated Photoredox Catalytic Arylation Reactions.

Authors:  Indrajit Ghosh; Leyre Marzo; Amrita Das; Rizwan Shaikh; Burkhard König
Journal:  Acc Chem Res       Date:  2016-08-02       Impact factor: 22.384

6.  Synthesis of gem-Difluoroallylboronates via FeCl2-Catalyzed Boration/β-Fluorine Elimination of Trifluoromethyl Alkenes.

Authors:  Yang Liu; Yuhan Zhou; Yilong Zhao; Jingping Qu
Journal:  Org Lett       Date:  2017-01-31       Impact factor: 6.005

7.  Lewis Acid Promoted Single C-F Bond Activation of the CF3 Group: SN 1'-Type 3,3-Difluoroallylation of Arenes with 2-Trifluoromethyl-1-alkenes.

Authors:  Kohei Fuchibe; Hibiki Hatta; Ken Oh; Rie Oki; Junji Ichikawa
Journal:  Angew Chem Int Ed Engl       Date:  2017-04-18       Impact factor: 15.336

8.  Radical Hydroarylation of Functionalized Olefins and Mechanistic Investigation of Photocatalytic Pyridyl Radical Reactions.

Authors:  Ciaran P Seath; David B Vogt; Zihao Xu; Allyson J Boyington; Nathan T Jui
Journal:  J Am Chem Soc       Date:  2018-11-05       Impact factor: 15.419

Review 9.  Multiplicity of mammalian reductases for xenobiotic carbonyl compounds.

Authors:  Toshiyuki Matsunaga; Shinichi Shintani; Akira Hara
Journal:  Drug Metab Pharmacokinet       Date:  2006-02       Impact factor: 3.614

10.  Fine-tuned organic photoredox catalysts for fragmentation-alkynylation cascades of cyclic oxime ethers.

Authors:  Franck Le Vaillant; Marion Garreau; Stefano Nicolai; Ganna Gryn'ova; Clemence Corminboeuf; Jerome Waser
Journal:  Chem Sci       Date:  2018-05-30       Impact factor: 9.825

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  9 in total

1.  Photoredox-Mediated Net-Neutral Radical/Polar Crossover Reactions.

Authors:  Rebecca J Wiles; Gary A Molander
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2.  Catalyzing the Hydrodefluorination of CF3-Substituted Alkenes by PhSiH3. H• Transfer from a Nickel Hydride.

Authors:  Chengbo Yao; Shuai Wang; Jack Norton; Matthew Hammond
Journal:  J Am Chem Soc       Date:  2020-01-24       Impact factor: 15.419

3.  Cross-Electrophile Coupling of Unactivated Alkyl Chlorides.

Authors:  Holt A Sakai; Wei Liu; Chi Chip Le; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2020-06-26       Impact factor: 15.419

4.  Nickel-Catalyzed Defluorinative Coupling of Aliphatic Aldehydes with Trifluoromethyl Alkenes.

Authors:  Jichao Xiao; John Montgomery
Journal:  ACS Catal       Date:  2022-02-03       Impact factor: 13.700

5.  Catalytic defluorinative ketyl-olefin coupling by halogen-atom transfer.

Authors:  Peter Bellotti; Huan-Ming Huang; Teresa Faber; Ranjini Laskar; Frank Glorius
Journal:  Chem Sci       Date:  2022-06-10       Impact factor: 9.969

6.  Synthesis of C6-Substituted Purine Nucleoside Analogues via Late-Stage Photoredox/Nickel Dual Catalytic Cross-Coupling.

Authors:  James J Perkins; Valerie W Shurtleff; Alayna M Johnson; Abdellatif El Marrouni
Journal:  ACS Med Chem Lett       Date:  2021-03-08       Impact factor: 4.345

7.  Developments in Photoredox-Mediated Alkylation for DNA-Encoded Libraries.

Authors:  Shivani Patel; Shorouk O Badir; Gary A Molander
Journal:  Trends Chem       Date:  2020-12-29

8.  Photoredox-mediated hydroalkylation and hydroarylation of functionalized olefins for DNA-encoded library synthesis.

Authors:  Shorouk O Badir; Alexander Lipp; Matthias Krumb; María Jesús Cabrera-Afonso; Lisa Marie Kammer; Victoria E Wu; Minxue Huang; Adam Csakai; Lisa A Marcaurelle; Gary A Molander
Journal:  Chem Sci       Date:  2021-08-05       Impact factor: 9.825

9.  Umpolung Difunctionalization of Carbonyls via Visible-Light Photoredox Catalytic Radical-Carbanion Relay.

Authors:  Shun Wang; Bei-Yi Cheng; Matea Sršen; Burkhard König
Journal:  J Am Chem Soc       Date:  2020-04-13       Impact factor: 15.419

  9 in total

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