期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 140, 期 22, 页码 6801-6805出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b04000
关键词
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资金
- National Basic Research Program of China [2015CB931900, 2016YFB0101200]
- National Natural Science Foundation of China [21632009, 21421002, 21472221]
- Chinese Academy of Sciences [KGZD-EW-T08]
- Key Research Program of Frontier Sciences of CAS [QYZDJ-SSW-SLH049]
- Shanghai Rising-Star Program [16QA1404600]
- Youth Innovation Promotion Association CAS [2014231]
Trifluoromethyl benzoate (TFBz) is developed as a new shelf-stable trifluoromethoxylation reagent, which can be easily prepared from inexpensive starting materials using KF as the only fluorine source. The synthetic potency of TFBz is demonstrated by trifluoromethoxylation halogenation of arynes, nucleophilic substitution of alkyl (pseudo)halides, cross-coupling with aryl stannanes, and asymmetric difunctionalization of alkenes. The unprecedented trifluoromethoxylation-halogenation of arynes proceeds smoothly at room temperature with the aid of a crown ether-complexed potassium cation, which significantly stabilizes the trifluoromethoxide anion derived from TFBz.
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