Literature DB >> 23463911

Room-temperature photoinduced direct C-H-arylation via base-promoted homolytic aromatic substitution.

María E Budén1, Javier F Guastavino, Roberto A Rossi.   

Abstract

Conceptually different approach toward biaryl syntheses by photoinduced direct C-H arylation of benzene and thiophene in the presence of t-BuOK is reported. The reaction proceeds through photo- and base-promoted homolytic aromatic substitution. The o-, m- and p- substituted ArI, as well as the electron-donating and electron-withdrawing nature of the substituents were found be good to excellent substrates. Heteroaryl, ArBr, ArCl and double C-H arylation were successfully achieved.

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Year:  2013        PMID: 23463911     DOI: 10.1021/ol3034687

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


  11 in total

1.  Scalable, Metal- and Additive-Free, Photoinduced Borylation of Haloarenes and Quaternary Arylammonium Salts.

Authors:  Adelphe M Mfuh; John D Doyle; Bhuwan Chhetri; Hadi D Arman; Oleg V Larionov
Journal:  J Am Chem Soc       Date:  2016-03-01       Impact factor: 15.419

Review 2.  The electron is a catalyst.

Authors:  Armido Studer; Dennis P Curran
Journal:  Nat Chem       Date:  2014-09       Impact factor: 24.427

3.  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

4.  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

5.  Organoboron chemistry comes to light: recent advances in photoinduced synthetic approaches to organoboron compounds.

Authors:  Viet D Nguyen; Vu T Nguyen; Shengfei Jin; Hang T Dang; Oleg V Larionov
Journal:  Tetrahedron       Date:  2018-12-24       Impact factor: 2.457

6.  Additive- and Metal-Free, Predictably 1,2- and 1,3-Regioselective, Photoinduced Dual C-H/C-X Borylation of Haloarenes.

Authors:  Adelphe M Mfuh; Vu T Nguyen; Bhuwan Chhetri; Jessica E Burch; John D Doyle; Vladimir N Nesterov; Hadi D Arman; Oleg V Larionov
Journal:  J Am Chem Soc       Date:  2016-07-01       Impact factor: 15.419

7.  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

8.  Thermally Induced Carbohydroxylation of Styrenes with Aryldiazonium Salts.

Authors:  Stephanie Kindt; Karina Wicht; Markus R Heinrich
Journal:  Angew Chem Int Ed Engl       Date:  2016-06-08       Impact factor: 15.336

9.  One-pot synthesis of Ag-Cu-Cu2O/C nanocomposites derived from a metal-organic framework as a photocatalyst for borylation of aryl halide.

Authors:  Dicky Annas; Shamim Ahmed Hira; Sehwan Song; Jong-Seong Bae; Sungkyun Park; Kang Hyun Park
Journal:  RSC Adv       Date:  2021-10-06       Impact factor: 4.036

10.  Efficient metal-free photochemical borylation of aryl halides under batch and continuous-flow conditions.

Authors:  Kai Chen; Shuai Zhang; Pei He; Pengfei Li
Journal:  Chem Sci       Date:  2016-02-01       Impact factor: 9.825

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