Synthesis and Properties of CF3(OCF3)CH‐Substituted Arenes and Alkenes

Summary of main observation and conclusion A silver‐mediated oxidative trifluoromethylation of easily accessible α‐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‐s...

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Bibliographic Details
Published in:Chinese journal of chemistry 2020-08, Vol.38 (8), p.847-854
Main Authors: Xu, Wen‐Qi, Xu, Xiu‐Hua, Qing, Feng‐Ling
Format: Article
Language:English
Subjects:
Alcohols
Alkene
Alkenes
Arene
Aromatic compounds
CF3‐derived motif
Fluoroalkyl alcohol
Lipophilic
Lipophilicity
Oxidative trifluoromethylation
Substitutes
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Summary:Summary of main observation and conclusion A silver‐mediated oxidative trifluoromethylation of easily accessible α‐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. A series of novel CF3(OCF3)CH‐substituted arenes and alkenes were prepared through the silver‐mediated oxidative trifluoromethylation of α‐trifluoromethyl alcohols. Evaluation of the lipophilicities indicated that this CH(OCF3)CF3 motif is more lipophilic than the common fluorine‐containing groups such as CF3, OCF3, and SCF3.
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.202000062