Literature DB >> 10810715

An efficient diamine.copper complex-catalyzed coupling of arylboronic acids with imidazoles

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Abstract

[formula: see text] A novel diamine.copper complex-catalyzed intermolecular coupling of arylboronic acids (1) with imidazoles (3) is described. In the presence of a catalytic amount of [Cu(OH).TMEDA]2Cl2 (2), arylboronic acids (1) react smoothly with imidazoles (3) in dichloromethane at room temperature to give a variety of N-arylimidazoles (4) in good to excellent yields.

Entities:  

Year:  2000        PMID: 10810715     DOI: 10.1021/ol000033j

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


  12 in total

Review 1.  Aerobic copper-catalyzed organic reactions.

Authors:  Scott E Allen; Ryan R Walvoord; Rosaura Padilla-Salinas; Marisa C Kozlowski
Journal:  Chem Rev       Date:  2013-06-20       Impact factor: 60.622

2.  Tuning the copper(II)/copper(I) redox potential for more robust copper-catalyzed C-N bond forming reactions.

Authors:  James D Cope; Henry U Valle; Ruby S Hall; Kathleen M Riley; Ekta Goel; Saborni Biswas; Michael P Hendrich; David O Wipf; Sean L Stokes; Joseph P Emerson
Journal:  Eur J Inorg Chem       Date:  2020-02-26       Impact factor: 2.524

3.  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

4.  Synthesis of a cyclic pentapeptide mimic of the active site His-Tyr cofactor of cytochrome c oxidase.

Authors:  Maximillian E Mahoney; Allen Oliver; Olöf Einarsdóttir; Joseph P Konopelski
Journal:  J Org Chem       Date:  2009-11-06       Impact factor: 4.354

5.  N-substituted imines by the copper-catalyzed N-imination of boronic acids and organostannanes with O-acyl ketoximes.

Authors:  Songbai Liu; Ying Yu; Lanny S Liebeskind
Journal:  Org Lett       Date:  2007-04-20       Impact factor: 6.005

6.  N-amidation by copper-mediated cross-coupling of organostannanes or boronic acids with o-acetyl hydroxamic acids.

Authors:  Zhihui Zhang; Ying Yu; Lanny S Liebeskind
Journal:  Org Lett       Date:  2008-06-17       Impact factor: 6.005

7.  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

8.  Palladium- and copper-mediated N-aryl bond formation reactions for the synthesis of biological active compounds.

Authors:  Carolin Fischer; Burkhard Koenig
Journal:  Beilstein J Org Chem       Date:  2011-01-14       Impact factor: 2.883

9.  New efficient ligand for sub-mol % copper-catalyzed C-N cross-coupling reactions running under air.

Authors:  Per-Fredrik Larsson; Peter Astvik; Per-Ola Norrby
Journal:  Beilstein J Org Chem       Date:  2012-11-09       Impact factor: 2.883

10.  Coupling of C-nitro-NH-azoles with arylboronic acids. A route to N-aryl-C-nitroazoles.

Authors:  Marta K Kurpet; Aleksandra Dąbrowska; Małgorzata M Jarosz; Katarzyna Kajewska-Kania; Nikodem Kuźnik; Jerzy W Suwiński
Journal:  Beilstein J Org Chem       Date:  2013-07-30       Impact factor: 2.883

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