期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 139, 期 33, 页码 11622-11628出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b07661
关键词
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资金
- Duke University
- National Institutes of Health [GM118786]
- CR Hauser Memorial fellowship
- GAANN fellowship
Arene amination is achieved by site-selective C-H zincation followed by copper-catalyzed coupling with O-benzoylhydroxylarnines under mild conditions. Key to this success is ortho-zincation mediated by lithium amidodiethylzincate base that is effective for a wide range of arenes, including nonactivated arenes bearing simple functionalities such as fluoride, chloride, ester,, amide, ether, nitrile, and trifluorometlryl groups as well as heteroarenes including iridole, thiophene, pyridine, and isoquinoline. An analogous C-H azidation is also accomplished using aiifloiodinarie for direct introduction of a useful azide group onto a broad scope of arenes and heteroarenes. These new transformations offer rapid access. to valuable and diverse chemical space of aminoarenes. Their broad applications in organic synthesis and drug discovery are demonstrated in the synthesis of novel analogues of natural product (-)-nicotine and antidepressant sertraline by late-stage amination and azidation reactions.
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