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Electrochemical Properties and Reactions of Organoboronic Acids in the Presence of Fluoride Ions
Author(s) -
Suzuki Junji,
Shida Naoki,
Inagi Shinsuke,
Fuchigami Toshio
Publication year - 2016
Publication title -
electroanalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.574
H-Index - 128
eISSN - 1521-4109
pISSN - 1040-0397
DOI - 10.1002/elan.201600130
Subject(s) - fluoride , ion , electrochemistry , chemistry , inorganic chemistry , alkyl , boron , organic chemistry , electrode
Electrochemical analyses of alkyl, phenyl, and thienylboronic acids were comparatively studied by cyclic voltammetric measurements in the absence and presence of fluoride ions, and we found remarkable negative shift of their oxidation potentials in the presence of fluoride ions compared with those in the absence of fluoride ions. Such negative shift seems to be derived from the formation of negative charged boron‐ate complex with fluoride ions. Anodic fluorination of 2‐acetyl‐5‐thienylboronic acid was carried out to provide mono‐ and trifluoro products eliminating a boryl group in moderate yields. These results clearly indicate that a boryl group with fluoride ions is a good electroauxiliary.