Literature DB >> 22839593

Palladium-catalyzed nitromethylation of aryl halides: an orthogonal formylation equivalent.

Ryan R Walvoord1, Simon Berritt, Marisa C Kozlowski.   

Abstract

An efficient cross-coupling reaction of aryl halides and nitromethane was developed with the use of parallel microscale experimentation. The arylnitromethane products are precursors for numerous useful synthetic products. An efficient method for their direct conversion to the corresponding oximes and aldehydes in a one-pot operation has been discovered. The process exploits inexpensive nitromethane as a carbonyl equivalent, providing a mild and convenient formylation method that is compatible with many functional groups.

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Year:  2012        PMID： 22839593      PMCID： PMC3430980          DOI： 10.1021/ol301713j

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


  13 in total

Review 1.  Conjugate additions of nitroalkanes to electron-poor alkenes: recent results.

Authors:  Roberto Ballini; Giovanna Bosica; Dennis Fiorini; Alessandro Palmieri; Marino Petrini
Journal:  Chem Rev       Date:  2005-03       Impact factor: 60.622

2.  A general and efficient method for the formylation of aryl and heteroaryl bromides.

Authors:  Stefan Klaus; Helfried Neumann; Alexander Zapf; Dirk Strübing; Sandra Hübner; Juan Almena; Thomas Riermeier; Peter Gross; Martin Sarich; Wolf-Rüdiger Krahnert; Kai Rossen; Matthias Beller
Journal:  Angew Chem Int Ed Engl       Date:  2005-12-16       Impact factor: 15.336

3.  Cascade formation of isoxazoles: facile base-mediated rearrangement of substituted oxetanes.

Authors:  Johannes A Burkhard; Boris H Tchitchanov; Erick M Carreira
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-28       Impact factor: 15.336

4.  Synthesis of unsymmetrical 3,4-diaryl-3-pyrrolin-2-ones utilizing pyrrole Weinreb amides.

Authors:  Jessica G Greger; Sarah J P Yoon-Miller; Nathan R Bechtold; Scott A Flewelling; Jacob P MacDonald; Catherine R Downey; Eric A Cohen; Erin T Pelkey
Journal:  J Org Chem       Date:  2011-09-26       Impact factor: 4.354

5.  Efficient palladium-catalyzed cross-coupling of highly acidic substrates, nitroacetates.

Authors:  Alison E Metz; Simon Berritt; Spencer D Dreher; Marisa C Kozlowski
Journal:  Org Lett       Date:  2012-01-20       Impact factor: 6.005

6.  Palladium-catalyzed monoarylation of nitroalkanes.

Authors:  Erasmus M Vogl; Stephen L Buchwald
Journal:  J Org Chem       Date:  2002-01-11       Impact factor: 4.354

7.  The first conversion of primary alkyl halides to nitroalkanes under aqueous medium.

Authors:  Roberto Ballini; Luciano Barboni; Guido Giarlo
Journal:  J Org Chem       Date:  2004-10-01       Impact factor: 4.354

8.  Synthesis and structure-activity relationship of 7-(substituted)-aminomethyl-4-quinolone-3-carboxylic acid derivatives.

Authors:  Zhenfa Zhang; Aizhen Yu; Weicheng Zhou
Journal:  Bioorg Med Chem       Date:  2007-08-24       Impact factor: 3.641

9.  Efficient cross-coupling of secondary alkyltrifluoroborates with aryl chlorides--reaction discovery using parallel microscale experimentation.

Authors:  Spencer D Dreher; Peter G Dormer; Deidre L Sandrock; Gary A Molander
Journal:  J Am Chem Soc       Date:  2008-06-27       Impact factor: 15.419

10.  Enantioselective alpha-arylation of ketones with aryl triflates catalyzed by difluorphos complexes of palladium and nickel.

Authors:  Xuebin Liao; Zhiqiang Weng; John F Hartwig
Journal:  J Am Chem Soc       Date:  2007-12-13       Impact factor: 15.419
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  8 in total

1.  Preparation of (-)-Nutlin-3 using enantioselective organocatalysis at decagram scale.

Authors:  Tyler A Davis; Anna E Vilgelm; Ann Richmond; Jeffrey N Johnston
Journal:  J Org Chem       Date:  2013-10-15       Impact factor: 4.354

2.  Nitroethylation of vinyl triflates and bromides.

Authors:  Rosaura Padilla-Salinas; Ryan R Walvoord; Sergei Tcyrulnikov; Marisa C Kozlowski
Journal:  Org Lett       Date:  2013-07-25       Impact factor: 6.005

3.  Accounting for Strong Ligand Sensitivity in Pd-Catalyzed α-Arylation of Enolates from Ketones, Esters, and Nitroalkanes.

Authors:  Sergei Tcyrulnikov; Marisa C Kozlowski
Journal:  J Org Chem       Date:  2020-02-12       Impact factor: 4.354

4.  2-Aryl-2-nitroacetates as central precursors to aryl nitromethanes, α-ketoesters, and α-amino acids.

Authors:  Alison E Metz; Marisa C Kozlowski
Journal:  J Org Chem       Date:  2013-01-02       Impact factor: 4.354

5.  Minimizing the amount of nitromethane in palladium-catalyzed cross-coupling with aryl halides.

Authors:  Ryan R Walvoord; Marisa C Kozlowski
Journal:  J Org Chem       Date:  2013-08-13       Impact factor: 4.354

6.  Highly Diastereoselective Michael Reactions Using β-Nitrocarbonyl Nucleophiles.

Authors:  Amber A S Gietter-Burch; Roxana E Mitrut; Donald A Watson
Journal:  Org Lett       Date:  2015-10-26       Impact factor: 6.005

7.  Copper-promoted site-selective carbonylation of sp3 and sp2 C-H bonds with nitromethane.

Authors:  Xuesong Wu; Jinmin Miao; Yanrong Li; Guigen Li; Haibo Ge
Journal:  Chem Sci       Date:  2016-04-26       Impact factor: 9.825

8.  Palladium-Catalyzed α-Arylation of Aryl Nitromethanes.

Authors:  Kelsey F VanGelder; Marisa C Kozlowski
Journal:  Org Lett       Date:  2015-11-20       Impact factor: 6.005
  8 in total

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