Literature DB >> 21688782

Selective ortho-bromination of substituted benzaldoximes using Pd-catalyzed C-H activation: application to the synthesis of substituted 2-bromobenzaldehydes.

Emmanuelle Dubost1, Christine Fossey, Thomas Cailly, Sylvain Rault, Frederic Fabis.   

Abstract

Substituted 2-bromobenzaldehydes were synthesized from benzaldehydes using a three-step sequence involving a selective palladium-catalyzed ortho-bromination as the key step. O-Methyloxime serves as a directing group in this reaction. A rapid deprotection of substituted 2-bromobenzaldoximes afforded substituted 2-bromobenzaldehydes with good overall yields.

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Year:  2011        PMID: 21688782     DOI: 10.1021/jo200853j

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  9 in total

1.  Modular, Metal-Catalyzed Cycloisomerization Approach to Angularly Fused Polycyclic Aromatic Hydrocarbons and Their Oxidized Derivatives.

Authors:  Paul F Thomson; Damon Parrish; Padmanava Pradhan; Mahesh K Lakshman
Journal:  J Org Chem       Date:  2015-07-21       Impact factor: 4.354

2.  X-ray Characterization and Structure-Based Optimization of Striatal-Enriched Protein Tyrosine Phosphatase Inhibitors.

Authors:  Michael R Witten; Lisa Wissler; Melanie Snow; Stefan Geschwindner; Jon A Read; Nicholas J Brandon; Angus C Nairn; Paul J Lombroso; Helena Käck; Jonathan A Ellman
Journal:  J Med Chem       Date:  2017-11-08       Impact factor: 7.446

3.  Regioselective Halogenation of 1,4-Benzodiazepinones via CH Activation.

Authors:  Hajer Abdelkafi; Jean-Christophe Cintrat
Journal:  Sci Rep       Date:  2015-07-16       Impact factor: 4.379

4.  Palladium-catalyzed ortho-halogenations of acetanilides with N-halosuccinimides via direct sp2 C-H bond activation in ball mills.

Authors:  Zi Liu; Hui Xu; Guan-Wu Wang
Journal:  Beilstein J Org Chem       Date:  2018-02-16       Impact factor: 2.883

5.  Transition-Metal-Free Decarboxylative Iodination: New Routes for Decarboxylative Oxidative Cross-Couplings.

Authors:  Gregory J P Perry; Jacob M Quibell; Adyasha Panigrahi; Igor Larrosa
Journal:  J Am Chem Soc       Date:  2017-08-08       Impact factor: 15.419

6.  Eco-friendly methoximation of aromatic aldehydes and ketones using MnCl2.4H2O as an easily accessible and efficient catalyst.

Authors:  Melina C Ontivero; Teodoro S Kaufman; Iván Cortés; Andrea B J Bracca
Journal:  R Soc Open Sci       Date:  2021-07-28       Impact factor: 2.963

7.  2-Bromo-5-fluoro-benzaldehyde.

Authors:  Robert E Tureski; Joseph M Tanski
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-07-13

8.  Ruthenium-Catalyzed meta-Selective C-H Bromination.

Authors:  Christopher J Teskey; Andrew Y W Lui; Michael F Greaney
Journal:  Angew Chem Int Ed Engl       Date:  2015-08-18       Impact factor: 15.336

9.  A convenient and eco-friendly cerium(III) chloride-catalysed synthesis of methoxime derivatives of aromatic aldehydes and ketones.

Authors:  Iván Cortés; Teodoro S Kaufman; Andrea B J Bracca
Journal:  R Soc Open Sci       Date:  2018-05-23       Impact factor: 2.963

  9 in total

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