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Synthesis of the novel ionic liquid [ N ‐pentylpyridinium] + [ closo ‐CB 11 H 12 ] − and its usage as a reaction medium in catalytic dehalogenation of aromatic halides
Author(s) -
Zhu Yinghuai,
Ching Chibun,
Carpenter Keith,
Xu Rong,
Selvaratnam Selvasothi,
Hosmane Narayan S.,
Maguire John A.
Publication year - 2003
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.407
Subject(s) - chemistry , yield (engineering) , halogenation , solvent , salt (chemistry) , melting point , palladium , nuclear magnetic resonance spectroscopy , catalysis , selectivity , medicinal chemistry , nuclear chemistry , spectroscopy , ionic liquid , stereochemistry , organic chemistry , materials science , metallurgy , physics , quantum mechanics
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.