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Issue 9, 2017
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Completing the series of boron-nucleophilic cyanoborates: boryl anions of type NHC–B(CN)2

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Abstract

Since the first seminal report of boron-centred nucleophiles, the area of boryl anions has developed only sporadically and requires further systematisation. The boryl anions of type NHC–B(CN)2 (NHC = N-heterocyclic carbene) described herein complete a consistent series with the known anions cAAC–B(CN)2 [cAAC = cyclic(alkyl)(amino)carbene] and B(CN)32−. A novel approach towards NHC-stabilised cyanoboranes based on alkylthio-cyano exchange at boron is presented, and in contrast to other methods affords the products in better purity and yield. Reduction of suitable NHC–dicyanoboranes gave two unprecedented examples of NHC–B(CN)2 boryl anions. The latter were shown to react as boron-centred nucleophiles with facile formation of B–E bonds, where E = C, Si, Sn, P, Au. Bonding analysis by DFT calculations suggests a systematic variation of the energy of the boron-centred HOMO depending on the carbene, which in turn can control the nucleophilic character.

Graphical abstract: Completing the series of boron-nucleophilic cyanoborates: boryl anions of type NHC–B(CN)2−

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Publication details

The article was received on 17 May 2017, accepted on 02 Jul 2017 and first published on 03 Jul 2017


Article type: Edge Article
DOI: 10.1039/C7SC02238G
Citation: Chem. Sci., 2017,8, 6274-6280
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    Completing the series of boron-nucleophilic cyanoborates: boryl anions of type NHC–B(CN)2

    R. Böser, L. C. Haufe, M. Freytag, P. G. Jones, G. Hörner and R. Frank, Chem. Sci., 2017, 8, 6274
    DOI: 10.1039/C7SC02238G

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