Substituent and Solvent Effects on the Reactions of Organoboronic Acids with Fluoride

The introduction of an electron-withdrawing substituent or a substituent protonated to be positively charged and potentially involved in hydrogen bonding enhances the reactivities of phenylboronic acids with fluoride. The use of a 60% aqueous MeOH medium suppresses the formation of the negatively ch...

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Published inBulletin of the Chemical Society of Japan Vol. 74; no. 3; pp. 509 - 510
Main Authors Yuchi, Akio, Tatebe, Atsushi, Kani, Shinpei, James, Tony D
Format Journal Article
LanguageEnglish
Published Tokyo The Chemical Society of Japan 01.03.2001
Chemical Society of Japan
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Summary:The introduction of an electron-withdrawing substituent or a substituent protonated to be positively charged and potentially involved in hydrogen bonding enhances the reactivities of phenylboronic acids with fluoride. The use of a 60% aqueous MeOH medium suppresses the formation of the negatively charged species, irrespective of whether their structures are trigonal or tetrahedral, but enhances the overall reactivity because of less solvation of fluoride.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.74.509