Literature DB >> 16819863

Highly selective room-temperature copper-catalyzed C-N coupling reactions.

Alexandr Shafir1, Stephen L Buchwald.   

Abstract

Through the use of cyclic beta-diketones as supporting ligands, the copper-catalyzed coupling of aryl iodides with aliphatic amines occurs at room temperature in as little as 1 h. These high reaction rates allow for the coupling of a wide range of aryl and heteroaryl iodides at room temperature. This method is highly tolerant of a number of reactive functional groups, including -Br and aromatic -NH2 as well as phenolic and aliphatic -OH. The high selectivity of the CuI-beta-diketone catalyst for aliphatic amines represents a useful complement to the palladium-based methods.

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Year:  2006        PMID: 16819863     DOI: 10.1021/ja063063b

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


  27 in total

1.  Cu(I)-amido complexes in the Ullmann reaction: reactions of Cu(I)-amido complexes with iodoarenes with and without autocatalysis by CuI.

Authors:  Ramesh Giri; John F Hartwig
Journal:  J Am Chem Soc       Date:  2010-10-26       Impact factor: 15.419

2.  Synthesis of indolines via a domino Cu-catalyzed amidation/cyclization reaction.

Authors:  Ana Minatti; Stephen L Buchwald
Journal:  Org Lett       Date:  2008-06-04       Impact factor: 6.005

3.  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

4.  Diamine Ligands in Copper-Catalyzed Reactions.

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

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.  Nickel-Catalyzed [2+2+2] Cycloaddition of Diynes and Cyanamides.

Authors:  Ryan M Stolley; Michael T Maczka; Janis Louie
Journal:  European J Org Chem       Date:  2011-07

7.  Copper-catalyzed arylation of 1H-perfluoroalkanes.

Authors:  Ilya Popov; Sergey Lindeman; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2011-05-31       Impact factor: 15.419

8.  Cu(II) complex of pyridine-based polydentate as a novel, efficient, and highly reusable catalyst in C-N bond-forming reaction.

Authors:  Hashem Sharghi; Saeideh Sepehri; Mahdi Aberi
Journal:  Mol Divers       Date:  2017-06-26       Impact factor: 2.943

9.  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

10.  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

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