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Issue 11, 2015
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Divergence from the classical hydroboration reactivity; boron containing materials through a hydroboration cascade of small cyclic dienes

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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

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Publication details

The article was received on 05 Sep 2014, accepted on 04 Aug 2015 and first published on 06 Aug 2015


Article type: Edge Article
DOI: 10.1039/C4SC02729A
Citation: Chem. Sci., 2015,6, 6262-6269
  • Open access: Creative Commons BY license
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    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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