Literature DB >> 10804566

Palladium-catalyzed coupling of vinylogous amides with aryl halides: applications to the synthesis of heterocycles

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Abstract

[formula: see text] Described herein is the first example of the palladium-catalyzed coupling of vinylogous amides with aryl bromides and chlorides. The scope of this reaction with respect to the aryl component is investigated. Additionally, a tandem reaction sequence in which the above coupling is followed by an intramolecular Heck reaction is presented. These reactions can be applied to high-yielding, one-pot syntheses of nitrogen-containing heterocycles.

Entities:  

Year:  2000        PMID: 10804566     DOI: 10.1021/ol000031z

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


  7 in total

1.  Dialkylbiaryl Phosphines in Pd-Catalyzed Amination: A User's Guide.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Chem Sci       Date:  2011       Impact factor: 9.825

Review 2.  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

3.  Multicomponent assembly of highly substituted indoles by dual palladium-catalyzed coupling reactions.

Authors:  John M Knapp; Jie S Zhu; Dean J Tantillo; Mark J Kurth
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-24       Impact factor: 15.336

4.  Microwave-assisted synthesis of 3-nitroindoles from N-aryl enamines via intramolecular arene-alkene coupling.

Authors:  Huy H Nguyen; Mark J Kurth
Journal:  Org Lett       Date:  2012-12-26       Impact factor: 6.005

5.  An intramolecular C-N cross-coupling of β-enaminones: a simple and efficient way to precursors of some alkaloids of Galipea officinalis.

Authors:  Hana Doušová; Radim Horák; Zdeňka Růžičková; Petr Šimůnek
Journal:  Beilstein J Org Chem       Date:  2015-05-27       Impact factor: 2.883

6.  Palladium-catalyzed C-N and C-O bond formation of N-substituted 4-bromo-7-azaindoles with amides, amines, amino acid esters and phenols.

Authors:  Rajendra Surasani; Dipak Kalita; A V Dhanunjaya Rao; K B Chandrasekhar
Journal:  Beilstein J Org Chem       Date:  2012-11-19       Impact factor: 2.883

7.  [6π] Photocyclization to cis-Hexahydrocarbazol-4-ones: Substrate Modification, Mechanism, and Scope.

Authors:  Sachin G Modha; Alexander Pöthig; Andreas Dreuw; Thorsten Bach
Journal:  J Org Chem       Date:  2019-01-23       Impact factor: 4.354

  7 in total

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