期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 57, 期 42, 页码 13795-13799出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201808495
关键词
arenes; photocatalysis; radicals; trifluoromethoxylating reagents; trifluoromethoxylation
资金
- NIH [R35GM119652]
- NSF [ACI-1053575, CHE-1654122]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R35GM119652] Funding Source: NIH RePORTER
The trifluoromethoxy (OCF3) radical is of great importance in organic chemistry. Yet, the catalytic and selective generation of this radical at room temperature and pressure remains a longstanding challenge. Herein, the design and development of a redox-active cationic reagent (1) that enables the formation of the OCF3 radical in a controllable, selective, and catalytic fashion under visible-light photocatalytic conditions is reported. More importantly, the reagent allows catalytic, intermolecular C-H trifluoromethoxylation of a broad array of (hetero)arenes and biorelevant compounds. Experimental and computational studies suggest single electron transfer (SET) from excited photoredox catalysts to 1 resulting in exclusive liberation of the OCF3 radical. Addition of this radical to (hetero)arenes gives trifluoromethoxylated cyclohexadienyl radicals that are oxidized and deprotonated to afford the products of trifluoromethoxylation.
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