1, 3‐Dehydro‐o‐Carborane: Generation and Reaction with Arenes1. Issue 32 (1st July 2014)

• Record Type: Journal Article
• Authors: Zhao, Da; Zhang, Jiji; Xie, Zuowei
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 32(2014)
• Page Start: 8488
• Page End: 8491
• Publication Date: 2014-07-01
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201405023
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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‐<italic>o</italic>‐carborane featuring a cage CB bond having multiple bonding characters, and is successfully generated by treatment of 3‐diazonium‐<italic>o</italic>‐carborane tetrafluoroborate with non‐nucleophilic bases. This presents a new methodology for simultaneous functionalization of both cage carbon and boron vertices.</p> </abstract>