C–H Triflation of BINOL Derivatives Using DIH and TfOH
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- Hironobu Nakazawa
- Department of Chemical Engineering, National Institute of Technology, Nara College, 22 Yata-cho, Yamatokoriyama, Nara 639-1080, Japan
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- Makoto Sako
- The Institute of Scientific and Industrial Research (ISIR), Osaka University, Mihogaoka, Ibaraki-shi, Osaka 567-0047, Japan
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- Yu Masui
- Department of Chemical Engineering, National Institute of Technology, Nara College, 22 Yata-cho, Yamatokoriyama, Nara 639-1080, Japan
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- Ryo Kurosaki
- Department of Chemical Engineering, National Institute of Technology, Nara College, 22 Yata-cho, Yamatokoriyama, Nara 639-1080, Japan
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- Shunya Yamamoto
- Department of Chemical Engineering, National Institute of Technology, Nara College, 22 Yata-cho, Yamatokoriyama, Nara 639-1080, Japan
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- Toshiyuki Kamei
- Department of Chemical Engineering, National Institute of Technology, Nara College, 22 Yata-cho, Yamatokoriyama, Nara 639-1080, Japan
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- Toyoshi Shimada
- Department of Chemical Engineering, National Institute of Technology, Nara College, 22 Yata-cho, Yamatokoriyama, Nara 639-1080, Japan
Description
C-H trifluoromethanesulfonyloxylation (triflation) of 1,1'-bi-2-naphthol (BINOL) derivatives has been established under mild conditions using 1,3-diiodo-5,5-dimethylhydantoin (DIH) and trifluoromethanesulfonic acid (TfOH). Up to eight TfO groups can be introduced in a single operation. The resulting highly oxidized BINOL derivatives can be successfully converted to 8,8'-dihydroxy BINOL and bisnaphthoquinone compounds. Mechanistic studies suggested that C-H triflation occurs in the form of an aromatic substitution reaction via the in situ formation of a radical cation.
Journal
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- Organic Letters
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Organic Letters 21 (16), 6466-6470, 2019-08-06
American Chemical Society (ACS)