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Ring lithiation and functionalization of imidazol-2-ylidene-boranes

Solovyev, A and Lacôte, E and Curran, DP (2011) Ring lithiation and functionalization of imidazol-2-ylidene-boranes. Organic Letters, 13 (22). 6042 - 6045. ISSN 1523-7060

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N,N′-Dialkyl and N,N′-diaryl imidazol-2-ylidene-boranes and trifluoroboranes are rapidly lithiated at C4 of the imidazole ring, and the resulting intermediates have been quenched with an assortment of electrophiles to provide ring-functionalized imidazol-2-ylidene-boranes. Further deprotonation and functionalization of C5 have been demonstrated. Deboronation of the products by treatment with triflic acid or iodine and then methanol opens a route to C4/C5 functionalized imidazolium salts and imidazol-2-ylidenes. © 2011 American Chemical Society.


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Item Type: Article
Status: Published
CreatorsEmailPitt UsernameORCID
Solovyev, A
Lacôte, E
Curran, DPcurran@pitt.eduCURRAN
Date: 18 November 2011
Date Type: Publication
Journal or Publication Title: Organic Letters
Volume: 13
Number: 22
Page Range: 6042 - 6045
DOI or Unique Handle: 10.1021/ol202516c
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1523-7060
PubMed ID: 22022887
Date Deposited: 15 Nov 2012 21:21
Last Modified: 02 Feb 2019 15:58


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