Issue 68, 2017

Stoichiometric and catalytic isomerization of alkenylboranes using bulky Lewis bases

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

Supplementary files

Article information

Article type
Communication
Submitted
28 jun. 2017
Accepted
03 ago. 2017
First published
03 ago. 2017

Chem. Commun., 2017,53, 9458-9461

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, 53, 9458 DOI: 10.1039/C7CC04904H

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