Recent advances in the chemistry of carborynes

• Generation of 1,2-dehydro-o-carboranes (o-carborynes) and 1,3-dehydro-o-carboranes.
• Reactivity patterns of carborynes and synthesis of functional o-carboranes.
• Reaction mechanisms.

Like the importance of benzyne in modern synthetic chemistry, 1,2-dehydro-o-carborane (o-carboryne), a three-dimensional relative of benzyne, has been utilized as a powerful synthon for generating a wide range of cage carbon functionalized o-carboranes over the past 25 years and a number of synthetically useful processes have been developed. Very recently, another reactive intermediate, 1,3-dehydro-o-carborane featuring a multiple cage C-B bond, has been reported for the applications in the selective functionalization of cage boron atom. These synthons are complimentary to each other in the functionalization of carboranes. This review offers an overview of recent advances in this interesting research field.

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