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

Anna Andreou; Michal Leskes; Pablo G. Jambrina; Gary J. Tustin; Clare P. Grey; Edina Rosta; Oren A. Scherman

doi:10.1039/c4sc02729a

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

Anna Andreou, Michal Leskes, Pablo G. Jambrina, Gary J. Tustin, Clare P. Grey, Edina Rosta, Oren A. Scherman^*

^*Corresponding author for this work

Chemistry

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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.

Original language	English
Pages (from-to)	6262-6269
Number of pages	8
Journal	Chemical Science
Volume	6
Issue number	11
Early online date	6 Aug 2015
DOIs	https://doi.org/10.1039/c4sc02729a
Publication status	E-pub ahead of print - 6 Aug 2015

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title = "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.",

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T1 - Divergence from the classical hydroboration reactivity; boron containing materials through a hydroboration cascade of small cyclic dienes

AU - Andreou, Anna

AU - Leskes, Michal

AU - Jambrina, Pablo G.

AU - Tustin, Gary J.

AU - Grey, Clare P.

AU - Rosta, Edina

AU - Scherman, Oren A.

PY - 2015/8/6

Y1 - 2015/8/6

N2 - 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.

AB - 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.

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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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