Literature DB >> 20450213

Mild silver(I)-mediated regioselective iodination and bromination of arylboronic acids.

Raed M Al-Zoubi1, Dennis G Hall.   

Abstract

A convenient and regioselective silver(I)-mediated electrophilic iodination and bromination reaction of arylboronic acids has been developed. The boronic acid does not require protection prior to the reaction, which can be performed on a multigram scale with moderate to excellent yields. A mild, simple, and effective method is disclosed to provide ortho-haloarylboronic acids that can be used as useful intermediates in selective sequential Suzuki-Miyaura cross-coupling reactions to provide ortho-triaryl derivatives in good yields.

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Year:  2010        PMID: 20450213     DOI: 10.1021/ol100537x

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


  6 in total

1.  An alternative to the Sandmeyer approach to aryl iodides.

Authors:  Bao Hu; William H Miller; Kiel D Neumann; Ethan J Linstad; Stephen G DiMagno
Journal:  Chemistry       Date:  2015-03-10       Impact factor: 5.236

2.  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

3.  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

4.  Boryl (Hetero)aryne Precursors as Versatile Arylation Reagents: Synthesis through C-H Activation and Orthogonal Reactivity.

Authors:  Emilien Demory; Karthik Devaraj; Andreas Orthaber; Paul J Gates; Lukasz T Pilarski
Journal:  Angew Chem Int Ed Engl       Date:  2015-08-13       Impact factor: 15.336

Review 5.  Sequential and iterative Pd-catalyzed cross-coupling reactions in organic synthesis.

Authors:  Patrick Dobrounig; Melanie Trobe; Rolf Breinbauer
Journal:  Monatsh Chem       Date:  2016-12-09       Impact factor: 1.451

6.  Boronic acid-DMAPO cooperative catalysis for dehydrative condensation between carboxylic acids and amines.

Authors:  Kazuaki Ishihara; Yanhui Lu
Journal:  Chem Sci       Date:  2015-11-06       Impact factor: 9.825

  6 in total

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