期刊
ACS CATALYSIS
卷 8, 期 6, 页码 5032-5037出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.8b01253
关键词
iron catalysis; trifluoromethyl amines; azides; olefins; N-heterocycles
资金
- Welch Foundation [AA-1846]
- National Institutes of Health [GM110382]
- Alfred P. Sloan Foundation [FG-2015-65240]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM110382] Funding Source: NIH RePORTER
We report herein an iron-catalyzed azidotri-fluoromethylation method for expedient vicinal trifluoromethyl primary-amine synthesis. This method is effective for a broad range of olefins and N-heterocycles, and it facilitates efficient synthesis of a wide variety of vicinal trifluoromethyl primary amines, including those that prove difficult to synthesize with existing approaches. Our preliminary mechanistic studies revealed that the catalyst-promoted azido-group transfer proceeds through a carbo-radical instead of a carbocation species. Characterization of an active iron catalyst through X-ray crystallographic studies suggests that structurally novel iron-azide complexes promote the oxidant activation and selective azido-group transfer
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