Concise Report
Synthesis and Properties of CF3(OCF3)CH-Substituted Arenes and Alkenes†
Wen-Qi Xu,
Xiu-Hua Xu,
Feng-Ling Qing,
Wen-Qi Xu
Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Science, Chinese Academy of Science, 345 Lingling Lu, Shanghai, 200032 China
Search for more papers by this authorXiu-Hua Xu
Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Science, Chinese Academy of Science, 345 Lingling Lu, Shanghai, 200032 China
Search for more papers by this authorCorresponding Author
Feng-Ling Qing
Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Science, Chinese Academy of Science, 345 Lingling Lu, Shanghai, 200032 China
Key Laboratory of Science and Technology of Eco-Textiles, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, 2999 North Renmin Lu, Shanghai, 201620 China
E-mail: [email protected]Search for more papers by this authorWen-Qi Xu,
Xiu-Hua Xu,
Feng-Ling Qing,
Wen-Qi Xu
Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Science, Chinese Academy of Science, 345 Lingling Lu, Shanghai, 200032 China
Search for more papers by this authorXiu-Hua Xu
Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Science, Chinese Academy of Science, 345 Lingling Lu, Shanghai, 200032 China
Search for more papers by this authorCorresponding Author
Feng-Ling Qing
Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Science, Chinese Academy of Science, 345 Lingling Lu, Shanghai, 200032 China
Key Laboratory of Science and Technology of Eco-Textiles, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, 2999 North Renmin Lu, Shanghai, 201620 China
E-mail: [email protected]Search for more papers by this author†Dedicated to the 70th Anniversary of Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences.
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.
Supporting Information
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Appendix S1: Supporting Information |
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