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

Chemical Communications : Chem Comm
Liu Leo LiuDouglas W Stephan

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-BrC6H42, p-MeC6H43). These species react with Ph3SnH to give [Mes3PH]+[RCOOB(C6F5)3]- (R = Ph 10, p-BrC6H411, p-MeC6H412) and (Ph3Sn)2. The mechanism of these SET reactions is discussed in light of control experiments and DFT calculations.

References

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Citations

Nov 15, 2018·Chemistry : a European Journal·Yizhu LiuKay Severin
Feb 7, 2019·Chemical Society Reviews·Liu Leo Liu, Douglas W Stephan
Apr 11, 2019·Angewandte Chemie·Elliot L BennettJ Chris Slootweg
Apr 11, 2019·Chemistry : a European Journal·Youngsuk KimDouglas W Stephan
Mar 10, 2020·Chemistry : a European Journal·Ryan Andrews, Douglas Wade Stephan
Feb 13, 2020·Chemistry : a European Journal·Crispin Lichtenberg
Aug 26, 2020·Angewandte Chemie·Chris SlootwegBas de Bruin
Mar 18, 2020·Chemistry : a European Journal·Helge LangeWolfram W Seidel
Apr 8, 2020·Chemistry : a European Journal·Flip HoltropJ Chris Slootweg
Sep 16, 2020·Angewandte Chemie·Ayan DasguptaRebecca L Melen
Jan 23, 2021·Organic & Biomolecular Chemistry·Gautam KumarIndranil Chatterjee
Jun 11, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·Yanlin PanTongdao Wang
Mar 20, 2020·Chemical Science·Yoshitaka AramakiTakashi Ooi
Oct 26, 2018·Journal of the American Chemical Society·Zhaowen DongThomas Müller
Jul 10, 2020·Inorganic Chemistry·Anthony WongGabriel Ménard
Dec 10, 2021·Chemistry : a European Journal·Max HasenbeckUrs Gellrich

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Methods Mentioned

BETA
NMR
X-ray

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