Lewis Acidity Enhancement of Triarylboranes via Peripheral Decoration with Cationic Groups
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The cationic boranes [Ar(N+)BMes(2)](+), [Ar(N+)(2)BMes](2+), and [Ar(N+)(3)B](3+) (Ar(N+) = [4-(Me(3)N)-2,6-Me(2)-C(6)H(2)](+); Mes = mesityl) have been synthesized and studied by cyclic voltammetry. The results obtained in this study show that the reduction potential of these derivatives in THF is increased by 0.36 V upon each substitution of a mesityl by a cationic Ar(N+) anilium group. Remarkably, the trication (3+), whose triflate salt is water soluble, complexes cyanide anions in pure water at pH 7. These properties underscore the dramatic effects caused by the increased number of cationic groups.
author list (cited authors)
Chiu, C., Kim, Y., & Gabba, F. P.
complete list of authors
Chiu, Ching-Wen||Kim, Youngmin||Gabbaï, François P