Mechanistic Studies on the Copper-Catalyzed N-Arylation of Amides
Name
Buchwald_Mechanistic studies.pdf
Size
5.01 MB
Format
Adobe PDF
Checksum (MD5)
ec39061d18b2145ce5e8f848987bad58
Author(s)
Strieter, Eric R.
Bhayana, Brijesh
Buchwald, Stephen Leffler
Date Issued
December 2008
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Strieter, Eric R., Brijesh Bhayana, and Stephen L. Buchwald. “Mechanistic Studies on the Copper-Catalyzed N-Arylation of Amides.” Journal of the American Chemical Society 131, no. 1 (January 14, 2009): 78-88.
Version
Author's final manuscript
Abstract
The copper-catalyzed N-arylation of amides, i.e., the Goldberg reaction, is an efficient method for the construction of products relevant to both industry and academic settings. Herein, we present mechanistic details concerning the catalytic and stoichiometric N-arylation of amides. In the context of the catalytic reaction, our findings reveal the importance of chelating diamine ligands in controlling the concentration of the active catalytic species. The consistency between the catalytic and stoichiometric results suggests that the activation of aryl halides occurs through a 1,2-diamine-ligated copper(I) amidate complex. Kinetic studies on the stoichiometric N-arylation of aryl iodides using 1,2-diamine ligated Cu(I) amidates also provide insights into the mechanism of aryl halide activation.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Terms of Use
Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.
Persistent DSpace Link
DOI of Published Version
https://doi.org/10.1021/ja0781893
