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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.