High Yielding Preparation of Dicarba-closo-dodecaboranes Using a Silver(I) Mediated Dehydrogenative Alkyne-Insertion Reaction

The synthesis of 1,2-dicarba-closo-dodecaboranes (ortho-carboranes) is often low yielding which is a critical issue given the increasing use of boron clusters in material science and medicinal chemistry. To address this barrier, a series of Cu, Ag, and Au salts were screened to identify compounds th...

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Bibliographic Details
Published in:Inorganic chemistry 2013-08, Vol.52 (15), p.8743-8749
Main Authors: Toppino, Antonio, Genady, Afaf R, El-Zaria, Mohamed E, Reeve, James, Mostofian, Fargol, Kent, Jeff, Valliant, John F
Format: Article
Language:English
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Summary:The synthesis of 1,2-dicarba-closo-dodecaboranes (ortho-carboranes) is often low yielding which is a critical issue given the increasing use of boron clusters in material science and medicinal chemistry. To address this barrier, a series of Cu, Ag, and Au salts were screened to identify compounds that would enhance the yields of ortho-caboranes produced when treating alkynes with B10H12(CH3CN)2. Using a variety of functionalized ligands including mono- and polyfunctional internal and terminal alkynes, significant increases in yield were observed when AgNO3 was used in catalytic amounts. AgNO3 appears to prevent unwanted reduction/hydroboration of the alkyne prior to carborane formation, and the process is compatible with aryl, halo, hydroxy, nitrile, carbamate, and carbonyl functionalized alkynes.
ISSN:0020-1669
1520-510X
DOI:10.1021/ic400928v