期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 139, 期 49, 页码 17707-17710出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b09582
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资金
- National Institutes of Health (National Institute of General Medical Sciences) [R01-GM109194]
- Alexander von Humboldt Foundation
- National Science Foundation [NSF-1531940]
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 degrees 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.
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