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Highly strained heterocycles constructed from boron-boron multiple bonds and heavy chalcogens

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Woollins_2016_ACIE_HighlyStrained_AAM.pdf (979.6Kb)
Date
25/04/2016
Author
Braunschweig, Holger
Constantinidis, Philipp
Dellermann, Theresa
Ewing, William C.
Fischer, Ingo
Hess, Merlin
Knight, Fergus Ross
Rempel, Anna
Schneider, Christoph
Ullrich, Stefan
Vargas, Alfredo
Woollins, J Derek
Keywords
Boron
Heterocycles
Multiple bonds
Selenium
Tellurium
QD Chemistry
DAS
BDC
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Abstract
The reactions of a diborene with elemental selenium or tellurium are shown to afford a diboraselenirane or diboratellurirane, respectively. These reactions are reminiscent of the sequestration of sub-valent oxygen and nitrogen in the formation of oxiranes and aziridines; however, such reactivity is not known between alkenes and the heavy chalcogens. While carbon is too electronegative to affect the reduction of elements of lower relative electronegativity, the highly reducing nature of the B=B double bond enables reactions with Se0 and Te0. The capacity of multiple bonds between boron to donate electron density is highlighted in reactions where diborynes behave as nucleophiles, attacking one of the two Te atoms of diaryltellurides, forming salts consisting of diboratellurenium cations and aryltelluride anions.
Citation
Braunschweig , H , Constantinidis , P , Dellermann , T , Ewing , W C , Fischer , I , Hess , M , Knight , F R , Rempel , A , Schneider , C , Ullrich , S , Vargas , A & Woollins , J D 2016 , ' Highly strained heterocycles constructed from boron-boron multiple bonds and heavy chalcogens ' , Angewandte Chemie International Edition , vol. 55 , no. 18 , pp. 5606–5609 . https://doi.org/10.1002/anie.201601691
Publication
Angewandte Chemie International Edition
Status
Peer reviewed
DOI
https://doi.org/10.1002/anie.201601691
ISSN
1433-7851
Type
Journal article
Rights
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://dx.doi.org/10.1002/anie.201601691
Description
H.B. acknowledges the generous financial support provided by an ERC Advanced Grant.
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  • University of St Andrews Research
URI
http://hdl.handle.net/10023/10552

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