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Issue 8, 2018
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Closely related yet different: a borylene and its dimer are non-interconvertible but connected through reactivity

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Abstract

The self-stabilizing, tetrameric cyanoborylene [(cAAC)B(CN)]4 (I, cAAC = 1-(2,6-diisopropylphenyl)-3,3,5,5-tetramethylpyrrolidin-2-ylidene) and its diborene relative, [(cAAC)(CN)B[double bond, length as m-dash]B(CN)(cAAC)] (II), both react with disulfides and diselenides to yield the corresponding cAAC-supported cyanoboron bis(chalcogenides). Furthermore, reactions of I or II with elemental sulfur and selenium in various stoichiometries provided access to a variety of cAAC-stabilized cyanoboron–chalcogen heterocycles, including a unique dithiaborirane, a diboraselenirane, 1,3-dichalcogena-2,4-diboretanes, 1,3,4-trichalcogena-2,5-diborolanes and a rare six-membered 1,2,4,5-tetrathia-3,6-diborinane. Stepwise addition reactions and solution stability studies provided insights into the mechanism of these reactions and the subtle differences in reactivity observed between I and II.

Graphical abstract: Closely related yet different: a borylene and its dimer are non-interconvertible but connected through reactivity

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Supplementary files

Article information


Submitted
06 Nov 2017
Accepted
02 Jan 2018
First published
04 Jan 2018

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2018,9, 2252-2260
Article type
Edge Article

Closely related yet different: a borylene and its dimer are non-interconvertible but connected through reactivity

D. Auerhammer, M. Arrowsmith, R. D. Dewhurst, T. Kupfer, J. Böhnke and H. Braunschweig, Chem. Sci., 2018, 9, 2252
DOI: 10.1039/C7SC04789D

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