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Completing the series of boron-nucleophilic cyanoborates: Boryl anions of type NHC-B(CN)

Chemical Science, ISSN: 2041-6539, Vol: 8, Issue: 9, Page: 6274-6280
2017
  • 30
    Citations
  • 0
    Usage
  • 17
    Captures
  • 1
    Mentions
  • 8
    Social Media
Metric Options:   Counts1 Year3 Year

Metrics Details

  • Citations
    30
  • Captures
    17
  • Mentions
    1
    • References
      1
      • Wikipedia
        1
  • Social Media
    8
    • Shares, Likes & Comments
      8
      • Facebook
        8

Article Description

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) (NHC = N-heterocyclic carbene) described herein complete a consistent series with the known anions cAAC-B(CN) [cAAC = cyclic(alkyl)(amino)carbene] and B(CN). 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) 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.

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