Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 49, Pages 15644-15648Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201709523
Keywords
amines; arenes; organocatalysis; photochemistry; synthetic methods
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Funding
- National Institutes of Health (NIGMS) [R01 GM120186]
- Eli Lilly Grantee Award
- American Australian Association
- UNC EFRC: Center for Solar Fuels, an Energy Frontier Research Center
- U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences [DE-SC0001011]
- National Institute of General Medical Sciences of the National Institutes of Health [R35GM118055]
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The direct catalytic C-H amination of arenes is a powerful synthetic strategy with useful applications in pharmaceuticals, agrochemicals, and materials chemistry. Despite the advances in catalytic C-H functionalization, the use of aliphatic amine coupling partners is limited. Described herein is the construction of C-N bonds, using primary amines, by direct C-H functionalization with an acridinium photoredox catalyst under an aerobic atmosphere. A wide variety of primary amines, including amino acids and more complex amines are competent coupling partners. Various electron-rich aromatics and heteroaromatics are useful scaffolds in this reaction, as are complex, biologically active arenes. We also describe the ability to functionalize arenes that are not oxidized by an acridinium catalyst, such as benzene and toluene, thus supporting a reactive amine cation radical intermediate.
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