title: 1,3-Dehydro-o-carborane: generation and reaction with arenes.
abstract: Like the importance of benzyne, witnessed in modern arene chemistry for decades, 1,2-dehydro-o-carborane (o-carboryne), a three-dimensional relative of benzyne, has been used as a synthon for generating a wide range of cage, carbon-functionalized carboranes over the past 20 years. However, the selective B functionalization of the cage still represents a challenging task. Disclosed herein is the first example of 1,3-dehydro-o-carborane featuring a cage C-B bond having multiple bonding characters, and is successfully generated by treatment of 3-diazonium-o-carborane tetrafluoroborate with non-nucleophilic bases. This presents a new methodology for simultaneous functionalization of both cage carbon and boron vertices.
authors.affiliation: Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin, N.T., Hong Kong (China).
authors.forename: Da
authors.initials: D
authors.lastname: Zhao
authors.forename: Jiji
authors.initials: J
authors.lastname: Zhang
authors.forename: Zuowei
authors.initials: Z
authors.lastname: Xie
keywords: boron; cage compounds; cycloaddition; ene reaction; multiple bonds