Electrochemical Properties and Reactions of Organoboronic Acids in the Presence of Fluoride Ions

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 i...

Full description

Saved in:
Bibliographic Details
Published inElectroanalysis (New York, N.Y.) Vol. 28; no. 11; pp. 2797 - 2801
Main Authors Suzuki, Junji, Shida, Naoki, Inagi, Shinsuke, Fuchigami, Toshio
Format Journal Article
LanguageEnglish
Published Blackwell Publishing Ltd 01.11.2016
Subjects
Anodic
Boron
Chemical reactions
Electroauxiliary
Electrochemical analysis
Electrochemical fluorination
Electrode potentials
Fluorides
Formations
Organoborate
Organoboronic acid
Phenyls
Online AccessGet full text

Cover

More Information
Summary: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.
Bibliography:istex:66BA3579EA053F07A0C525B9817F6213C32F7B32
Shibaura Institute of Technology
ArticleID:ELAN201600130
ark:/67375/WNG-MC0DGT9W-B
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1040-0397
1521-4109
DOI:10.1002/elan.201600130