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
- 30Citations
- 17Captures
- 1Mentions
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Metrics Details
- Citations30
- Citation Indexes30
- CrossRef30
- 25
- Captures17
- Readers17
- 17
- Mentions1
- References1
- Wikipedia1
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.
Bibliographic Details
http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=85027858308&origin=inward; http://dx.doi.org/10.1039/c7sc02238g; http://www.ncbi.nlm.nih.gov/pubmed/28989661; https://xlink.rsc.org/?DOI=C7SC02238G; http://xlink.rsc.org/?DOI=C7SC02238G; http://pubs.rsc.org/en/content/articlepdf/2017/SC/C7SC02238G; https://dx.doi.org/10.1039/c7sc02238g; https://pubs.rsc.org/en/content/articlelanding/2017/sc/c7sc02238g
Royal Society of Chemistry (RSC)
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