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N-heterocyclic carbene boranes are good hydride donors

Horn, M and Mayr, H and Lacôte, E and Merling, E and Deaner, J and Wells, S and McFadden, T and Curran, DP (2012) N-heterocyclic carbene boranes are good hydride donors. Organic Letters, 14 (1). 82 - 85. ISSN 1523-7060

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Abstract

The nucleophilicity parameters (N) of 1,3-bis(2,6-diisopropylphenyl) imidazol-2-ylidene borane and 1,3-dimethylimidazol-2-ylidene borane are 9.55 and 11.88. This places N-heterocyclic carbene boranes (NHC-boranes) among the most nucleophilic classes of neutral hydride donors. Reductions of highly electron-poor C=N and C=C bonds provide hydrogenation products along with new, stable borylated products. The results suggest that NHC-boranes have considerable untapped potential as neutral organic reductants. © 2011 American Chemical Society.

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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Horn, M
Mayr, H
Lacôte, E
Merling, E
Deaner, J
Wells, S
McFadden, T
Curran, DPcurran@pitt.eduCURRAN
Date: 6 January 2012
Date Type: Publication
Journal or Publication Title: Organic Letters
Volume: 14
Number: 1
Page Range: 82 - 85
DOI or Unique Handle: 10.1021/ol202836p
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1523-7060
PubMed ID: 22149270
Date Deposited: 20 Mar 2013 16:46
Last Modified: 15 Oct 2017 06:55
URI: http://d-scholarship.pitt.edu/id/eprint/17796

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