期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 37, 页码 16076-16082出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202004116
关键词
arenes; C-O activation; cross-coupling; nickel; synthetic methods
资金
- National Natural Science Foundation of China [21991121, 21421002]
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
- Office of Basic Energy Sciences of the U.S. Department of Energy [DE-SC0009363]
The increasing pharmaceutical importance of trifluoromethylarenes has stimulated the development of more efficient trifluoromethylation reactions. Tremendous efforts have focused on copper- and palladium-mediated/catalyzed trifluoromethylation of aryl halides. In contrast, no general method exists for the conversion of widely available inert electrophiles, such as phenol derivatives, into the corresponding trifluoromethylated arenes. Reported herein is a practical nickel-mediated trifluoromethylation of phenol derivatives with readily available trimethyl(trifluoromethyl)silane (TMSCF3). The strategy relies on PMe3-promoted oxidative addition and transmetalation, and CCl3CN-induced reductive elimination. The broad utility of this transformation has been demonstrated through the direct incorporation of trifluoromethyl into aromatic and heteroaromatic systems, including biorelevant compounds.
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