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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Abstract

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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Details

Item Type:	Article
Status:	Published
Creators/Authors:	Creators Email Pitt Username ORCID Solovyev, A Lacôte, E Curran, DP curran@pitt.edu CURRAN
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
URI:	http://d-scholarship.pitt.edu/id/eprint/16242

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