Literature DB >> 23688041

Visible-light photoredox in homolytic aromatic substitution: direct arylation of arenes with aryl halides.

Yannan Cheng1, Xiangyong Gu, Pixu Li.   

Abstract

Direct arylation of unactivated arenes or heteroarenes with aryl halides could be carried out in the presence of potassium tert-butoxide and dimethyl sulfoxide under visible-light irradiation. Ir(ppy)3 was found to be an effective photoredox catalyst for this reaction. The reactions of aryl iodides occurred at room temperature. Elevated temperature was required for aryl bromides. Homolytic aromatic substitution was proposed to be the operative reaction pathway.

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Year:  2013        PMID： 23688041     DOI： 10.1021/ol400946k

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  13 in total

1.  Nickel or phenanthroline mediated intramolecular arylation of sp3 C-H bonds using aryl halides.

Authors:  William C Wertjes; Lydia C Wolfe; Peter J Waller; Dipannita Kalyani
Journal:  Org Lett       Date:  2013-11-20       Impact factor: 6.005

2.  Phenyl hydrazine as initiator for direct arene C-H arylation via base promoted homolytic aromatic substitution.

Authors:  Abhishek Dewanji; Sandip Murarka; Dennis P Curran; Armido Studer
Journal:  Org Lett       Date:  2013-11-19       Impact factor: 6.005

3.  Photoredox catalysis powered by triplet fusion upconversion: arylation of heteroarenes.

Authors:  Jorge Castellanos-Soriano; Daniel Álvarez-Gutiérrez; M Consuelo Jiménez; Raúl Pérez-Ruiz
Journal:  Photochem Photobiol Sci       Date:  2022-03-18       Impact factor: 4.328

4.  Nickel-Mediated Synthesis of Isoindolinones at Room Temperature.

Authors:  William C Wertjes; Peter J Waller; Kyle E Shelton; Dipannita Kalyani
Journal:  Synthesis (Stuttg)       Date:  2014-08-21       Impact factor: 3.157

5.  Potent Reductants via Electron-Primed Photoredox Catalysis: Unlocking Aryl Chlorides for Radical Coupling.

Authors:  Nicholas G W Cowper; Colleen P Chernowsky; Oliver P Williams; Zachary K Wickens
Journal:  J Am Chem Soc       Date:  2020-01-17       Impact factor: 15.419

6.  Pd(II)-Catalyzed C3-Selective Arylation of Pyridine with (Hetero)arenes.

Authors:  Guo-Lin Gao; Wujiong Xia; Pankaj Jain; Jin-Quan Yu
Journal:  Org Lett       Date:  2016-02-02       Impact factor: 6.005

Review 7.  Photoredox-Catalyzed C-H Functionalization Reactions.

Authors:  Natalie Holmberg-Douglas; David A Nicewicz
Journal:  Chem Rev       Date:  2021-09-29       Impact factor: 60.622

8.  Reactivity of highly Lewis acidic diborane(4) towards pyridine and isocyanide: formation of boraalkene-pyridine complex and ortho-functionalized pyridine derivatives.

Authors:  Yuhei Katsuma; Hiroki Asakawa; Makoto Yamashita
Journal:  Chem Sci       Date:  2017-12-11       Impact factor: 9.825

9.  N-Acyloxyphthalimides as nitrogen radical precursors in the visible light photocatalyzed room temperature C-H amination of arenes and heteroarenes.

Authors:  Laura J Allen; Pablo J Cabrera; Melissa Lee; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2014-04-04       Impact factor: 15.419

10.  Charge-transfer-directed radical substitution enables para-selective C-H functionalization.

Authors:  Gregory B Boursalian; Won Seok Ham; Anthony R Mazzotti; Tobias Ritter
Journal:  Nat Chem       Date:  2016-06-06       Impact factor: 24.427
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