Synthesis of the novel ionic liquid [N-pentylpyridinium]+ [closo-CB11H12]− and its usage as a reaction medium in catalytic dehalogenation of aromatic halides

✍ Scribed by Yinghuai Zhu; Chibun Ching; Keith Carpenter; Rong Xu; Selvasothi Selvaratnam; Narayan S. Hosmane; John A. Maguire

• Publisher: John Wiley and Sons
• Year: 2003
• Tongue: English
• Weight: 124 KB
• Volume: 17
• Category: Article
• ISSN: 0268-2605
• DOI: 10.1002/aoc.407

✦ Synopsis

Abstract

The novel, low‐melting‐point (19 °C) salt [N‐pentylpyridinium]^+^ [closo‐CB~11~H~12~]^−^ (2) was synthesized in 93% yield and characterized by elemental analysis, IR spectroscopy, and ^1^H, ^13^C, and ^11^B NMR spectroscopy. The salt was used as a solvent in several dehalogenation reactions of mono‐ and poly‐chlorides and ‐bromides, catalyzed by the palladium complexes PdCl~2~(PPh~3~)~2~, PdCl~2~(dppe), and PdCl~2~(dppf). Complete debromination of C~6~Br~6~, 1,2,4,5‐tetrabromobenzene, C~60~Br~8~, and C~60~Br~24~ was accomplished quite rapidly, whereas dechlorination of 1,2,4‐trichlorobenzene proceeded more slowly, but with excellent products selectivity. Copyright © 2003 John Wiley & Sons, Ltd.