936951-92-7Relevant articles and documents
Palladium-catalyzed amination of 2-Iodo-para-carborane
Beletskaya, Irina P.,Bregadze, Vladimir I.,Kabytaev, Kuanysh Z.,Zhigareva, Galina G.,Petrovskii, Pavel V.,Glukhov, Ivan V.,Starikova, Zoya A.
, p. 2340 - 2347 (2008/10/09)
The palladium-catalyzed Buchwald-Hartwig amination of B-iodocarborane by various azoles and amines is described for the first time. The reactions of 2-iodo-p-carborane with indole, imidazole, benzimidazole, or carbazole in the system Pd(dba)2-BINAP-ButONa in dioxane at 100 °C gave 2-p-carboranyl derivatives of these azoles in high yields together with 2-hydroxy-p-carborane as a side product. The reactions of 2-iodo-p-carborane with aromatic amines in the same system gave the amination products in 60-70% yields and also were accompanied by the formation of hydroxy derivatives (up to 30% yields). In a special investigation it was shown that the base Bu tONa was responsible for its formation. The principle possibility of the amination of 2-iodo-p-carborane by morpholine (with 30% yield) as an example of aliphatic amination was shown. The structures of N-(1,12-dicarba-closo- dodecaboran-2-yl)carbazole (1), N-(1, 12-dicarba-closo-dodecaboran-2-yl) benzimidazole (2), N-(1, 12-dicarba-closo-dodecaboran-2-yl)indole (4), and 2-hydroxy-1,12-dicarba-closo-dodecaborane (5) have been established by X-ray diffraction studies.
