Issue 11, 2015

Divergence from the classical hydroboration reactivity; boron containing materials through a hydroboration cascade of small cyclic dienes

Abstract

The hydroboration 1,3- and 1,4-cyclic dienes has been systematically investigated. The behavior of such dienes towards mono and dihydroboration was monitored directly by 11B NMR to identify the actual boron species formed, as opposed to the most common analysis of the resultant oxidation products. Quantitative dihydroboration was achieved for the full range of cyclic dienes investigated including dienes, which were previously reported to be resistant to dihydroboration, leading to the formation of new boron-containing polymeric materials. The conditions favoring dihydroboration are reported as well as full characterisation of the materials. Furthermore, a hydroboration cascade mechanism is proposed for the formation of such boron-containing polymers, supported by both experimental and theoretical data.

Graphical abstract: Divergence from the classical hydroboration reactivity; boron containing materials through a hydroboration cascade of small cyclic dienes

Supplementary files

Article information

Article type
Edge Article
Submitted
05 Sep 2014
Accepted
04 Aug 2015
First published
06 Aug 2015
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2015,6, 6262-6269

Divergence from the classical hydroboration reactivity; boron containing materials through a hydroboration cascade of small cyclic dienes

A. Andreou, M. Leskes, P. G. Jambrina, G. J. Tustin, C. P. Grey, E. Rosta and O. A. Scherman, Chem. Sci., 2015, 6, 6262 DOI: 10.1039/C4SC02729A

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