Literature DB >> 11777446

Palladium-catalyzed monoarylation of nitroalkanes.

Erasmus M Vogl1, Stephen L Buchwald.   

Abstract

A general protocol for the Pd-catalyzed-arylation of nitroalkanes is described. Substituted aryl bromides as well as aryl chlorides can be coupled efficiently with a variety of nitroalkanes under mild conditions to selectively yield the monoarylated products. This method tolerates a number of functional groups including ketones, esters, and olefins. Notably, the arylation of nitroalkanes can be effected chemoselectively over ketone and ester arylation.

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Year:  2002        PMID: 11777446     DOI: 10.1021/jo010953v

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


  16 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.  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

3.  Trifluoromethylation of Secondary Nitroalkanes.

Authors:  Amber A S Gietter-Burch; Vijayarajan Devannah; Donald A Watson
Journal:  Org Lett       Date:  2017-05-23       Impact factor: 6.005

4.  Nickel-Catalyzed C-Alkylation of Nitroalkanes with Unactivated Alkyl Iodides.

Authors:  Sina Rezazadeh; Vijayarajan Devannah; Donald A Watson
Journal:  J Am Chem Soc       Date:  2017-06-08       Impact factor: 15.419

5.  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

6.  Organocatalytic Insertion of Isatins into Aryl Difluoronitromethyl Ketones.

Authors:  Ransheng Ding; Pegah R Bakhshi; Christian Wolf
Journal:  J Org Chem       Date:  2017-01-09       Impact factor: 4.354

Review 7.  Biaryl phosphane ligands in palladium-catalyzed amination.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

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

Authors:  Ryan R Walvoord; Simon Berritt; Marisa C Kozlowski
Journal:  Org Lett       Date:  2012-07-27       Impact factor: 6.005

9.  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

10.  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

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