Journal
CHINESE JOURNAL OF CHEMISTRY
Volume 38, Issue 8, Pages 847-854Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cjoc.202000062
Keywords
Oxidative trifluoromethylation; Fluoroalkyl alcohol; CF3-derived motif; Arene; Alkene; Lipophilicity
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Funding
- National Natural Science Foundation of China [21421002, 21991211]
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
- Youth Innovation Promotion Association CAS [2016234]
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The Summary of main observation and conclusion A silver-mediated oxidative trifluoromethylation of easily accessible alpha-trifluoromethyl alcohols with TMSCF3 was developed to access novel CF3(OCF3)CH-containing compounds. Deprotonation of CF3(OCF3)CH-substituted arenes afforded synthetically useful CF3O-substituted gem-difluoroalkenes. Furthermore, evaluation of the lipophilicities (log P) indicated that CH(OCF3)CF3 is more lipophilic than the common fluorinated motifs such as CF3, OCF3, and SCF3, thus rendering the CH(OCF3)CF3 motif appealing in drug discovery.
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