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- Title
Boron as a Powerful Reductant: Synthesis of a Stable Boron-Centered Radical-Anion Radical-Cation Pair.
- Authors
Bissinger, Philipp; Braunschweig, Holger; Damme, Alexander; Hörl, Christian; Krummenacher, Ivo; Kupfer, Thomas
- Abstract
Despite the fundamental importance of radical-anion radical-cation pairs in single-electron transfer (SET) reactions, such species are still very rare and transient in nature. Since diborenes have highly electron-rich BB double bonds, which makes them strong neutral reductants, we envisaged a possible realization of a boron-centered radical-anion radical-cation pair by SET from a diborene to a borole species, which are known to form stable radical anions upon one-electron reduction. However, since the reduction potentials of all know diborenes ( E1/2=−1.05/−1.55 V) were not sufficiently negative to reduce MesBC4Ph4 ( E1/2=−1.69 V), a suitable diborene, I iPr⋅( iPr)BB( iPr)⋅I iPr, was tailor-made to comply with these requirements. With a halfwave potential of E1/2=−1.95 V, this diborene ranks amongst the most powerful neutral organic reductants known and readily reacted with MesBC4Ph4 by SET to afford a stable boron-centered radical-anion radical-cation pair.
- Subjects
BORON; BORENIUM ions; PROTON transfer reactions; SINGLE electron devices; RADICAL ions
- Publication
Angewandte Chemie International Edition, 2015, Vol 54, Issue 1, p359
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201409513