Highly strained heterocycles constructed from boron-boron multiple bonds and heavy chalcogens
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
ISSN
1433-7851Type
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.Collections
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