Substitution Reactions at Tetracoordinate Boron: Synthesis of N-Heterocyclic Carbene Boranes with Boron−Heteroatom Bonds
In: Journal of the American Chemical Society, Jg. 132 (2010-10-01), S. 15072-15080
Online
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Zugriff:
Boryl halide, carboxylate and sulfonate complexes of 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene (dipp-Imd-BH(2)X, X = halide or sulfonate) have been prepared from the parent borane dipp-Imd-BH(3) by (1) substitution reactions with R-X (X = halide or sulfonate), (2) reactions with electrophiles (like I(2) or NIS), or (3) acid/base reactions with HX (provided that HX has a pK(a) of about 2 or less). Dipp-Imd-BH(2)I is most conveniently prepared by reaction with diiodine while dipp-Imd-BH(2)OTf 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.).
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Substitution Reactions at Tetracoordinate Boron: Synthesis of N-Heterocyclic Carbene Boranes with Boron−Heteroatom Bonds
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Autor/in / Beteiligte Person: | Lacôte, Emmanuel ; Chu, Qianli ; Curran, Dennis P. ; Malacria, Max ; Geib, Steven J. ; Solovyev, Andrey ; Fensterbank, Louis |
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Zeitschrift: | Journal of the American Chemical Society, Jg. 132 (2010-10-01), S. 15072-15080 |
Veröffentlichung: | American Chemical Society (ACS), 2010 |
Medientyp: | unknown |
ISSN: | 1520-5126 (print) ; 0002-7863 (print) |
DOI: | 10.1021/ja107025y |
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