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 Jan 2017
Accepted
03 Pha 2017
First published
03 Pha 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements