Literature DB >> 12296734

The copper-catalyzed N-arylation of indoles.

Jon C Antilla1, Artis Klapars, Stephen L Buchwald.   

Abstract

A general method for the N-arylation of indoles using catalysts derived from CuI and trans-1,2-cyclohexanediamine (1a), trans-N,N'-dimethyl-1,2-cyclohexanediamine (2a), or N,N'-dimethyl-ethylenediamine (3) is reported. N-Arylindoles can be produced in high yield from the coupling of an aryl iodide or aryl bromide with a variety of indoles.

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Year:  2002        PMID： 12296734     DOI： 10.1021/ja027433h

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  27 in total

1.  Scalable total syntheses of N-linked tryptamine dimers by direct indole-aniline coupling: psychotrimine and kapakahines B and F.

Authors:  Timothy Newhouse; Chad A Lewis; Kyle J Eastman; Phil S Baran
Journal:  J Am Chem Soc       Date:  2010-05-26       Impact factor: 15.419

2.  Copper complexes of anionic nitrogen ligands in the amidation and imidation of aryl halides.

Authors:  Jesse W Tye; Zhiqiang Weng; Adam M Johns; Christopher D Incarvito; John F Hartwig
Journal:  J Am Chem Soc       Date:  2008-07-03       Impact factor: 15.419

3.  Diamine Ligands in Copper-Catalyzed Reactions.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Chem Sci       Date:  2010       Impact factor: 9.825

4.  3-substituted indazoles as configurationally locked 4EGI-1 mimetics and inhibitors of the eIF4E/eIF4G interaction.

Authors:  Revital Yefidoff-Freedman; Ting Chen; Rupam Sahoo; Limo Chen; Gerhard Wagner; Jose A Halperin; Bertal H Aktas; Michael Chorev
Journal:  Chembiochem       Date:  2014-01-23       Impact factor: 3.164

5.  Computational explorations of mechanisms and ligand-directed selectivities of copper-catalyzed Ullmann-type reactions.

Authors:  Gavin O Jones; Peng Liu; K N Houk; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2010-05-05       Impact factor: 15.419

6.  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

7.  Mechanistic studies on the copper-catalyzed N-arylation of amides.

Authors:  Eric R Strieter; Brijesh Bhayana; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-01-14       Impact factor: 15.419

8.  Enantioselective Intermolecular C-O Bond Formation in the Desymmetrization of Diarylmethines Employing a Guanidinylated Peptide-Based Catalyst.

Authors:  Alex J Chinn; Byoungmoo Kim; Yongseok Kwon; Scott J Miller
Journal:  J Am Chem Soc       Date:  2017-11-27       Impact factor: 15.419

9.  Orthogonal Cu- and Pd-based catalyst systems for the O- and N-arylation of aminophenols.

Authors:  Debabrata Maiti; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-12-02       Impact factor: 15.419

10.  Pyrrole-2-carboxylic acid as a ligand for the Cu-catalyzed reactions of primary anilines with aryl halides.

Authors:  Ryan A Altman; Kevin W Anderson; Stephen L Buchwald
Journal:  J Org Chem       Date:  2008-06-11       Impact factor: 4.354
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