Copper-Catalyzed Amination of Aryl Chlorides under Mild Reaction Conditions
Name
nihms-2059365.pdf
Description
Accepted version
Size
1.83 MB
Format
Adobe PDF
Checksum (MD5)
a13e7049d9e9437805187e1730a4e73e
Author(s)
Ai, Han-Jun
Kim, Seoung-Tae
Liu, Cecilia
Buchwald, Stephen L
Date Issued
September 16, 2024
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society
Citation
Copper-Catalyzed Amination of Aryl Chlorides under Mild Reaction Conditions. Han-Jun Ai, Seoung-Tae Kim, Cecilia Liu, and Stephen L. Buchwald. Journal of the American Chemical Society 2024 146 (38), 25949-25955.
Version
Author's final manuscript
Abstract
We report a mild method for the copper-catalyzed amination of aryl chlorides. Key to the success of the method was the use of highly sterically encumbered N1,N2-diaryl diamine ligands which resist catalyst deactivation, allowing reactions to proceed at significantly lower temperatures and with a broader scope than current protocols. A sequence of highly chemoselective C-N and C-O cross-coupling reactions were demonstrated, and mechanistic studies indicate that oxidative addition of the Cu catalyst to the aryl chlorides is rate-limiting. We anticipate that the design principles disclosed herein will help motivate further advances in Cu-catalyzed transformations of aryl chlorides.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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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.
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DOI of Published Version
10.1021/jacs.4c10237
