Highly strained heterocycles constructed from boron-boron multiple bonds and heavy chalcogens
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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.
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 in English , vol 55 , no. 18 , 5606–5609 . DOI: 10.1002/anie.201601691
Angewandte Chemie International Edition in English
© 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
H.B. acknowledges the generous financial support provided by an ERC Advanced Grant.
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