Synthesis of 3-Aryl--carboranes with Sensitive Functional Groups.

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