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