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Homolytic cleavage of peroxide bonds via a single electron transfer of a frustrated Lewis pair

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Abstract

Single electron transfer (SET) reactions are effected by the combination of a Mes3P/B(C6F5)3 frustrated Lewis pair with benzoyl peroxide derivatives. The resulting homolytic cleavage of the peroxide bonds affords the radical salts [Mes3P˙]+[RCOOB(C6F5)3] (R = Ph 1, p-BrC6H4 2, p-MeC6H4 3). These species react with Ph3SnH to give [Mes3PH]+[RCOOB(C6F5)3] (R = Ph 10, p-BrC6H4 11, p-MeC6H4 12) and (Ph3Sn)2. The mechanism of these SET reactions is discussed in light of control experiments and DFT calculations.

Graphical abstract: Homolytic cleavage of peroxide bonds via a single electron transfer of a frustrated Lewis pair

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Publication details

The article was received on 02 May 2018, accepted on 14 May 2018 and first published on 14 May 2018


Article type: Communication
DOI: 10.1039/C8CC03522A
Citation: Chem. Commun., 2018, Advance Article
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    Homolytic cleavage of peroxide bonds via a single electron transfer of a frustrated Lewis pair

    L. L. Liu, L. L. Cao, D. Zhu, J. Zhou and D. W. Stephan, Chem. Commun., 2018, Advance Article , DOI: 10.1039/C8CC03522A

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