Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2015 Mar 16;54(12):3768-72.
doi: 10.1002/anie.201500404. Epub 2015 Feb 25.

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

Rebecca A Green  1 , John F Hartwig
Affiliations

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

Rebecca A Green et al. Angew Chem Int Ed Engl. .

Abstract

The nickel-catalyzed amination of aryl chlorides to form primary arylamines occurs with ammonia or ammonium sulfate and a well-defined single-component nickel(0) precatalyst containing a Josiphos ligand and an η(2)-bound benzonitrile ligand. This system also catalyzes the coupling of aryl chlorides with gaseous amines in the form of their hydrochloride salts.

Keywords: amination; ammonia; arylation; cross-coupling; nickel.

PubMed Disclaimer

Figures

Figure 1
Figure 1
ORTEP Structure of (PPF-tBu)Ni(η2-NCPh). Ellipsoids shown at 50% probability, hydrogen atoms omitted for clarity.
Scheme 1
Scheme 1
Radical clock experiments
See this image and copyright information in PMC

References

    1. Ricci A. Modern Amination Methods. Wiley-VCH Verlag GmbH; Weinheim: 2000.
    1. Kunz K, Scholz U, Ganzer D. Synlett. 2003:2428–2439.
    1. Ge S, Green RA, Hartwig JF. J. Am. Chem. Soc. 2014;136:1617–1627. - PMC - PubMed
    1. Borzenko A, Rotta-Loria NL, MacQueen PM, Lavoie CM, McDonald R, Stradiotto M. Angew. Chem. Int. Ed. 2015 DOI: 10.1002/ange.201410875. - PubMed
    1. Wolfe JP, Buchwald SL. J. Am. Chem. Soc. 1997;119:6054–6058.

Publication types