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Substitution reactions at tetracoordinate boron: Synthesis of N-heterocyclic carbene boranes with boron-heteroatom bonds

Solovyev, A and Chu, Q and Geib, SJ and Fensterbank, L and Malacria, M and Lacôte, E and Curran, DP (2010) Substitution reactions at tetracoordinate boron: Synthesis of N-heterocyclic carbene boranes with boron-heteroatom bonds. Journal of the American Chemical Society, 132 (42). 15072 - 15080. ISSN 0002-7863

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Abstract

Boryl halide, carboxylate and sulfonate complexes of 1,3-bis(2,6- diisopropylphenyl)imidazol-2-ylidene (dipp-Imd-BH2X, X = halide or sulfonate) have been prepared from the parent borane dipp-Imd-BH3 by (1) substitution reactions with R-X (X = halide or sulfonate), (2) reactions with electrophiles (like I2 or NIS), or (3) acid/base reactions with HX (provided that HX has a pKa of about 2 or less). Dipp-Imd-BH 2I is most conveniently prepared by reaction with diiodine while dipp-Imd-BH2OTf is best prepared by reaction with triflic acid. These and other less reactive complexes behave as electrophiles and can be substituted by a wide range of heteroatom nucleophiles including halides, thiolates and other sulfur-based nucleophiles, isocyanate, azide, nitrite, and cyanide. The resulting products are remarkably stable, and many have been characterized by X-ray crystallography. Several are members of very rare classes of functionalized boron compounds (boron azide, nitro compound, nitrous ester, etc.). © 2010 American Chemical Society.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Solovyev, A
Chu, Q
Geib, SJgeib@pitt.eduGEIB0000-0002-9160-7857
Fensterbank, L
Malacria, M
Lacôte, E
Curran, DPcurran@pitt.eduCURRAN
Date: 27 October 2010
Date Type: Publication
Journal or Publication Title: Journal of the American Chemical Society
Volume: 132
Number: 42
Page Range: 15072 - 15080
DOI or Unique Handle: 10.1021/ja107025y
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0002-7863
PubMed ID: 20886852
Date Deposited: 08 Feb 2013 21:00
Last Modified: 02 Feb 2019 15:58
URI: http://d-scholarship.pitt.edu/id/eprint/17258

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