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Stoichiometric and catalytic isomerization of alkenylboranes using bulky Lewis bases

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Abstract

1,1-Carboboration of alkynes with boranes R′B(C6F5)2 (R′ = (CH2)3Ph, C6F5) affords mixtures of the E and Z isomers of RCH = CR′B(C6F5)2 (R = (CH2)2Me, (CH2)3Me, (CH2)2Ph, CH2CHMe2, CHMe2, CMe3, CH2OMe, CH2N(CO)2C6H4), treatment of these alkenylboranes with stoichiometric or catalytic amounts of tBu2PH or other donors are shown to induce isomerization. The proposed mechanism involving a zwitterionic borataalkene intermediate is supported by computations.

Graphical abstract: Stoichiometric and catalytic isomerization of alkenylboranes using bulky Lewis bases

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Publication details

The article was received on 28 Jun 2017, accepted on 03 Aug 2017 and first published on 03 Aug 2017


Article type: Communication
DOI: 10.1039/C7CC04904H
Citation: Chem. Commun., 2017, Advance Article
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    Stoichiometric and catalytic isomerization of alkenylboranes using bulky Lewis bases

    F. A. Tsao, A. Sathaseevan, H. Zhu, S. Grimme, G. Erker and D. W. Stephan, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7CC04904H

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