Literature DB >> 19637871

Palladium-catalyzed aromatic C-H halogenation with hydrogen halides by means of electrochemical oxidation.

Fumitoshi Kakiuchi1, Takuya Kochi, Hitoshi Mutsutani, Noboru Kobayashi, Seiya Urano, Mitsuo Sato, Shigeru Nishiyama, Takamasa Tanabe.   

Abstract

A new strategy for catalytic functionalization of C-H bonds by means of electrochemical oxidation is described. Combination of palladium-catalyzed aromatic C-H bond cleavage and halogenation with electrochemically generated halonium ions enables highly efficient, selective halogenations of aromatic compounds in a green-sustainable manner. The required reagents for this reaction are an arene and an aqueous hydrogen halide as substrates, a palladium salt as a catalyst, and an organic solvent. No further additives such as electrolytes, oxidants, or ligands are necessary to achieve effective catalytic activity. Several remarkable advantages of the use of the electrochemical method are also described.

Entities:  

Year:  2009        PMID: 19637871     DOI: 10.1021/ja9049228

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  22 in total

1.  On the mechanism of palladium-catalyzed aromatic C-H oxidation.

Authors:  David C Powers; Daphne Y Xiao; Matthias A L Geibel; Tobias Ritter
Journal:  J Am Chem Soc       Date:  2010-10-20       Impact factor: 15.419

2.  Palladium-Catalyzed C-H Bond Acetoxylation via Electrochemical Oxidation.

Authors:  Anuska Shrestha; Melissa Lee; Anna L Dunn; Melanie S Sanford
Journal:  Org Lett       Date:  2017-12-22       Impact factor: 6.005

3.  Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance.

Authors:  Ming Yan; Yu Kawamata; Phil S Baran
Journal:  Chem Rev       Date:  2017-10-09       Impact factor: 60.622

4.  Pd(II)-catalyzed C-H iodination using molecular I2 as the sole oxidant.

Authors:  Xiao-Chen Wang; Yi Hu; Samuel Bonacorsi; Yang Hong; Richard Burrell; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2013-07-09       Impact factor: 15.419

Review 5.  Bystanding F+ oxidants enable selective reductive elimination from high-valent metal centers in catalysis.

Authors:  Keary M Engle; Tian-Sheng Mei; Xisheng Wang; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2011-01-24       Impact factor: 15.336

6.  A general strategy toward aromatic 1,2-ambiphilic synthons: palladium-catalyzed ortho-halogenation of PyDipSi-arenes.

Authors:  Alexander S Dudnik; Natalia Chernyak; Chunhui Huang; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-08       Impact factor: 15.336

7.  Ligand-Enabled Pd(II)-Catalyzed Bromination and Iodination of C(sp3)-H Bonds.

Authors:  Ru-Yi Zhu; Tyler G Saint-Denis; Ying Shao; Jian He; Joshua D Sieber; Chris H Senanayake; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2017-04-13       Impact factor: 15.419

8.  The Pyridyldiisopropylsilyl Group: A Masked Functionality and Directing Group for Monoselective ortho-Acyloxylation and ortho-Halogenation Reactions of Arenes.

Authors:  Chunhui Huang; Natalia Chernyak; Alexander S Dudnik; Vladimir Gevorgyan
Journal:  Adv Synth Catal       Date:  2011-05-01       Impact factor: 5.837

Review 9.  Palladium-catalyzed ligand-directed C-H functionalization reactions.

Authors:  Thomas W Lyons; Melanie S Sanford
Journal:  Chem Rev       Date:  2010-02-10       Impact factor: 60.622

10.  Twofold unsymmetrical C-H functionalization of PyrDipSi-substituted arenes: a general method for the synthesis of substituted meta-halophenols.

Authors:  Dhruba Sarkar; Ferdinand S Melkonyan; Anton V Gulevich; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2013-08-22       Impact factor: 15.336

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