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Copper-Catalyzed Alkylation of Aliphatic Amines Induced by Visible Light

Matier, Carson D. and Schwaben, Jonas and Peters, Jonas C. and Fu, Gregory C. (2017) Copper-Catalyzed Alkylation of Aliphatic Amines Induced by Visible Light. Journal of the American Chemical Society, 139 (49). pp. 17707-17710. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20171128-135738544

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Abstract

Although the alkylation of an amine by an alkyl halide serves as a “textbook example” of a nucleophilic substitution reaction, the selective mono-alkylation of aliphatic amines by unactivated, hindered halides persists as a largely unsolved challenge in organic synthesis. We report herein that primary aliphatic amines can be cleanly mono-alkylated by unactivated secondary alkyl iodides in the presence of visible light and a copper catalyst. The method operates under mild conditions (–10 °C), displays good functional-group compatibility, and employs commercially available catalyst components. A trapping experiment with TEMPO is consistent with C–N bond formation via an alkyl radical in an out-of-cage process.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/jacs.7b09582DOIArticle
http://pubs.acs.org/doi/10.1021/jacs.7b09582PublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/jacs.7b09582PublisherSupporting Information
ORCID:
AuthorORCID
Peters, Jonas C.0000-0002-6610-4414
Fu, Gregory C.0000-0002-0927-680X
Additional Information:© 2017 American Chemical Society. Received: September 7, 2017; Published: November 28, 2017. Support has been provided by the National Institutes of Health (National Institute of General Medical Sciences, grant R01-GM109194) and the Alexander von Humboldt Foundation (fellowship for J.S.). We thank Jun Myun Ahn, Bradley J. Gorsline, Dr. Paul H. Oyala (Caltech EPR Facility, supported by National Science Foundation grant NSF-1531940), Dr. Mona Shahgholi (Caltech Mass Spectrometry Facility), Dr. Yichen Tan, Dr. David G. VanderVelde (Caltech NMR Facility), and Dr. Scott C. Virgil (Caltech Center for Catalysis and Chemical Synthesis) for assistance and helpful discussions. The authors declare no competing financial interest.
Funders:
Funding AgencyGrant Number
NIHR01-GM109194
Alexander von Humboldt FoundationUNSPECIFIED
NSFCHE-1531940
Issue or Number:49
Record Number:CaltechAUTHORS:20171128-135738544
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20171128-135738544
Official Citation:Copper-Catalyzed Alkylation of Aliphatic Amines Induced by Visible Light. Carson D. Matier, Jonas Schwaben, Jonas C. Peters, and Gregory C. Fu. Journal of the American Chemical Society 2017 139 (49), 17707-17710. DOI: 10.1021/jacs.7b09582
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:83538
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:28 Nov 2017 22:18
Last Modified:03 Oct 2019 19:07

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