1,3‐Dehydro‐ o ‐Carborane: Generation and Reaction with Arenes | Zendy

Zhao Da | Zendy; Zhang Jiji | Zendy; Xie Zuowei | Zendy

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1,3‐Dehydro‐ o ‐Carborane: Generation and Reaction with Arenes

Author(s) -

Zhao Da,

Zhang Jiji,

Xie Zuowei

Publication year - 2014

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201405023

Subject(s) - carborane , aryne , synthon , chemistry , surface modification , nucleophile , boron , cage , combinatorial chemistry , carbon fibers , stereochemistry , medicinal chemistry , organic chemistry , materials science , catalysis , mathematics , combinatorics , composite number , composite material

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 CB 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.

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