Catalytic Amidation of 9-Iodo-m-carborane and 2-Iodo-p-carborane at a Boron Atom

The palladium-catalyzed amidation of B-iodocarboranes by various amides is described for the first time. The reactions of 2-iodo-1,12-dicarba-closo-dodecaborane (2-iodo-p-carborane) with acetamide, 2-pyrrolidinone, caprolactam, p-methylbenzamide, and 2-phenylacetamide using the system Pd(dba)2/BINAP...

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Bibliographic Details
Published in:Organometallics 2008-11, Vol.27 (22), p.5937-5942
Main Authors: Mukhin, Sergey N, Kabytaev, Kuanysh Z, Zhigareva, Galina G, Glukhov, Ivan V, Starikova, Zoya A, Bregadze, Vladimir I, Beletskaya, Irina P
Format: Article
Language:English
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Summary:The palladium-catalyzed amidation of B-iodocarboranes by various amides is described for the first time. The reactions of 2-iodo-1,12-dicarba-closo-dodecaborane (2-iodo-p-carborane) with acetamide, 2-pyrrolidinone, caprolactam, p-methylbenzamide, and 2-phenylacetamide using the system Pd(dba)2/BINAP/NaH (dba = dibenzylideneacetone; BINAP = rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl) in dioxane at 100 °C gave 2-p-carboranyl derivatives of these amides in good to high yields. Similar reactions of 9-iodo-1,7-dicarba-closo-dodecaborane (9-iodo-m-carborane) with corresponding amides afforded 9-m-carboranyl derivatives in good to high yields. The structures of N-(1,12-dicarba-closo-dodecaboran-2-yl)pyrrolidin-2-one (5), N-(1,7-dicarba-closo-dodecaboran-9-yl)acetamide (6), and N-(1,7-dicarba-closo-dodecaboran-9-yl)-2-phenylacetamide (7) have been established by X-ray diffraction studies.
ISSN:0276-7333
1520-6041
DOI:10.1021/om800635d