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C-H Triflation of BINOL Derivatives Using DIH and TfOH
Hironobu Nakazawa1, Makoto Sako2, Yu Masui1
1Department of Chemical Engineering, National Institute of Technology , Nara College , 22 Yata-cho , Yamatokoriyama , Nara 639-1080 , Japan.
Abstract:
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.
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