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Two new approaches to the functionalization of the 1-carba- closo -decaborate anion [1-CB 9 H 10 ] - at boron atoms via the ring-opening of its 1,4-dioxane derivative with various nucleophiles and Pd-catalysed cross-coupling of its iodo derivative with aromatic amines and heteroaromatics were developed.

A simple and efficient method was developed for the one-pot synthesis of 3-aryl derivatives of ortho -carborane with sensitive functional groups using 3-iodo- ortho -carborane and aryl zinc bromides that were generated in situ. A series of 3-aryl- ortho -carboranes, including those containing nitrile and ester groups, 3-RC 6 H 4 -1,2-C 2 B 10 H 11 (R = p -Me, p -NMe 2 , p -OCH 2 OMe, p -OMe, o -CN, p -CN, o -COOEt, m -COOEt, p -COOEt) was synthesized using this approach. The solid-state structures of 3-RC 6 H 4 -1,2-C 2 B 10 H 11 (R = p -OMe, o -CN, and p -CN) were determined by single crystal X-ray diffraction. The intramolecular hydrogen bonding involving the ortho -substituents of the aryl ring and the CH and BH groups of carborane was discussed.