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Issue 22, 2019
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Nucleophilic substitution: a facile strategy for selective B–H functionalization of carboranes

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Abstract

Vertex-specific functionalization of carboranes has received considerable research interest, due to the valuable application of carborane derivatives in medicine, coordination/organometallic chemistry and materials. In comparison with a protic cage C–H bond, cage B–H is hydridic and generally less polar, with a bond dissociation energy of ca. 108 kcal mol−1. These features make B–H activation quite different from that of the C–H bond. In addition, selectivity among ten very similar BH vertices in o-carborane is challenging yet crucial to the effective construction of carborane-based functional molecules. To address these issues, a brand new strategy of cage B–H nucleophilic substitution has recently been presented and developed for straightforward and regioselective cage B–H functionalization. The regioselectivity can be controlled by the electronic/steric properties of the cage carbon substituents. This Frontier article highlights the recent advancement in the nucleophilic cage B–H substitution of carboranes.

Graphical abstract: Nucleophilic substitution: a facile strategy for selective B–H functionalization of carboranes

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Article information


Submitted
16 Mar 2019
Accepted
16 Apr 2019
First published
17 Apr 2019

Dalton Trans., 2019,48, 7494-7498
Article type
Frontier

Nucleophilic substitution: a facile strategy for selective B–H functionalization of carboranes

Y. Quan, C. Tang and Z. Xie, Dalton Trans., 2019, 48, 7494
DOI: 10.1039/C9DT01140D

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