Literature DB >> 19322847

A general palladium-catalyzed amination of aryl halides with ammonia.

Thomas Schulz1, Christian Torborg, Stephan Enthaler, Benjamin Schäffner, Andreas Dumrath, Anke Spannenberg, Helfried Neumann, Armin Börner, Matthias Beller.   

Abstract

A new robust palladium/phosphine catalyst system for the selective monoarylation of ammonia with different aryl bromides and chlorides has been developed. The active catalyst is formed in situ from [Pd(OAc)(2)] and air- and moisture-stable phosphines as easy-to-handle pre-catalysts. The productivity of the catalyst system is comparable to that of competitive Pd/phosphine systems; full conversion is achieved with most substrates with 1-2 mol % of Pd source and a fourfold excess of ligand (L).

Entities:  

Year:  2009        PMID: 19322847     DOI: 10.1002/chem.200802678

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  11 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.  Catalytic organometallic reactions of ammonia.

Authors:  Jessica L Klinkenberg; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2011-01-03       Impact factor: 15.336

3.  Nickel-catalyzed amination of aryl chlorides with ammonia or ammonium salts.

Authors:  Rebecca A Green; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2015-02-25       Impact factor: 15.336

4.  Slow reductive elimination from arylpalladium parent amido complexes.

Authors:  Jessica L Klinkenberg; John F Hartwig
Journal:  J Am Chem Soc       Date:  2010-09-01       Impact factor: 15.419

5.  Palladium-catalyzed coupling of ammonia with aryl chlorides, bromides, iodides, and sulfonates: a general method for the preparation of primary arylamines.

Authors:  Giang D Vo; John F Hartwig
Journal:  J Am Chem Soc       Date:  2009-08-12       Impact factor: 15.419

6.  Mild and highly selective palladium-catalyzed monoarylation of ammonia enabled by the use of bulky biarylphosphine ligands and palladacycle precatalysts.

Authors:  Chi Wai Cheung; David S Surry; Stephen L Buchwald
Journal:  Org Lett       Date:  2013-07-01       Impact factor: 6.005

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.  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

9.  Palladium-catalyzed regiodivergent hydroaminocarbonylation of alkenes to primary amides with ammonium chloride.

Authors:  Bao Gao; Guoying Zhang; Xibing Zhou; Hanmin Huang
Journal:  Chem Sci       Date:  2017-10-24       Impact factor: 9.825

10.  Ligand-Controlled Palladium-Catalyzed Carbonylation of Alkynols: Highly Selective Synthesis of α-Methylene-β-Lactones.

Authors:  Yao Ge; Fei Ye; Jiawang Liu; Ji Yang; Anke Spannenberg; Haijun Jiao; Ralf Jackstell; Matthias Beller
Journal:  Angew Chem Int Ed Engl       Date:  2020-09-17       Impact factor: 15.336

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