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Electrochemical Oxidation of Organotrifluoroborate Compounds
Author(s) -
Suzuki Junji,
Tanigawa Masahiro,
Inagi Shinsuke,
Fuchigami Toshio
Publication year - 2016
Publication title -
chemelectrochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.182
H-Index - 59
ISSN - 2196-0216
DOI - 10.1002/celc.201600451
Subject(s) - electrochemistry , chemistry , anode , moiety , anodic oxidation , cyclic voltammetry , yield (engineering) , platinum , aryl , inorganic chemistry , organic chemistry , electrode , materials science , catalysis , metallurgy , alkyl
Electrochemical analyses of various organotrifluoroborates, and the corresponding boronic acids and esters, were comparatively studied by using cyclic voltammetry. The organotrifluoroborates were found to have much lower oxidation potentials compared with the latter two types of compounds. We also found a pronounced β‐effect for allyltrifluoroborate, which was indicated by both experimental and theoretical aspects. Such a β‐effect is similar to that of allyltrimethylsilane. Anodic oxidation of n ‐decyltrifluoroborate at a platinum anode gave a radical coupling product in moderate yield, eliminating a boryl moiety. Anodic acetoxylation of phenethyl‐, aryl‐, and styryltrifluoroborates was also successfully carried out at a graphite anode in NaOAc/AcOH to provide the acetoxylated products in good to moderate yields although a large excess of electricity was required.