1311297-00-3Relevant academic research and scientific papers
Insight into the role of the counteranion of an imidazolium salt in organocatalysis: A combined experimental and computational study
Wei, Siping,Wei, Xi-Guang,Su, Xiaoyu,You, Jingsong,Ren, Yi
experimental part, p. 5965 - 5971 (2011/07/08)
N-Heterocyclic carbenes (NHCs) can serve as very reactive nucleophilic catalysts and exhibit strong basicity. Herein, we initiate a combined experimental and computational investigation of the NHC-catalyzed ring-closing reactions of 4-(2-formylphenoxy)but
Substitution reactions at tetracoordinate boron: Synthesis of N-heterocyclic carbene boranes with boron-heteroatom bonds
Solovyev, Andrey,Chu, Qianli,Geib, Steven J.,Fensterbank, Louis,Malacria, Max,Lacote, Emmanuel,Curran, Dennis P.
supporting information; experimental part, p. 15072 - 15080 (2011/01/10)
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.).
