Literature DB >> 10814458

Efficient palladium-catalyzed N-arylation of indoles.

D W Old1, M C Harris, S L Buchwald.   

Abstract

[equation--see text] The N-arylation of indoles, including a variety of substituted ones, has been carried out using bulky, electron-rich phosphines as the supporting ligand in combination with Pd(2)(dba)(3). Using this catalyst system, the efficient coupling of indole and a variety of substituted indoles with aryl iodides, bromides, chlorides, and triflates can be achieved.

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Year:  2000        PMID: 10814458     DOI: 10.1021/ol005728z

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


  16 in total

1.  Palladium-catalyzed synthesis of N-vinyl pyrroles and indoles.

Authors:  Mohammad Movassaghi; Alison E Ondrus
Journal:  J Org Chem       Date:  2005-10-14       Impact factor: 4.354

2.  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

3.  Palladium-catalyzed amination of unprotected halo-7-azaindoles.

Authors:  Jaclyn L Henderson; Sarah M McDermott; Stephen L Buchwald
Journal:  Org Lett       Date:  2010-10-15       Impact factor: 6.005

4.  Palladium-catalyzed indole, pyrrole, and furan arylation by aryl chlorides.

Authors:  Enrico T Nadres; Anna Lazareva; Olafs Daugulis
Journal:  J Org Chem       Date:  2010-12-30       Impact factor: 4.354

5.  Pd-Catalyzed Alkene Carboheteroarylation Reactions for the Synthesis of 3-Cyclopentylindole Derivatives.

Authors:  Janelle K Kirsch; Jenna L Manske; John P Wolfe
Journal:  J Org Chem       Date:  2018-10-10       Impact factor: 4.354

6.  Phosphine-free palladium-catalyzed C-H bond arylation of free (N-H)-indoles and pyrroles.

Authors:  Xiang Wang; Denis V Gribkov; Dalibor Sames
Journal:  J Org Chem       Date:  2007-02-16       Impact factor: 4.354

Review 7.  Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions.

Authors:  Paula Ruiz-Castillo; Stephen L Buchwald
Journal:  Chem Rev       Date:  2016-09-30       Impact factor: 60.622

8.  PIII /PV =O Catalyzed Cascade Synthesis of N-Functionalized Azaheterocycles.

Authors:  Trevor V Nykaza; Gen Li; Junyu Yang; Michael R Luzung; Alexander T Radosevich
Journal:  Angew Chem Int Ed Engl       Date:  2020-01-29       Impact factor: 15.336

9.  Completely N1-selective palladium-catalyzed arylation of unsymmetric imidazoles: application to the synthesis of nilotinib.

Authors:  Satoshi Ueda; Mingjuan Su; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2011-12-14       Impact factor: 15.419

10.  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

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