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

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

doi:10.1002/aoc.407

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

Yinghuai Zhu^*, Chibun Ching, Keith Carpenter, Rong Xu, Selvasothi Selvaratnam, Narayan S. Hosmane, John A. Maguire

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

55 Citations (Scopus)

Abstract

The novel, low-melting-point (19 °C) salt [N-pentylpyridinium]⁺ [closo-CB₁₁H₁₂]^- (2) was synthesized in 93% yield and characterized by elemental analysis, IR spectroscopy, and ¹H, ¹³C, and ¹¹B 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 PdCl₂(PPh₃)₂, PdCl₂(dppe), and PdCl₂(dppf). Complete debromination of C₆Br₆, 1,2,4,5-tetrabromobenzene, C₆₀Br₈, and C₆₀Br₂₄ was accomplished quite rapidly, whereas dechlorination of 1,2,4-trichlorobenzene proceeded more slowly, but with excellent products selectivity.

Original language	English
Pages (from-to)	346-350
Number of pages	5
Journal	Applied Organometallic Chemistry
Volume	17
Issue number	6-7
DOIs	https://doi.org/10.1002/aoc.407
Publication status	Published - 2003
Externally published	Yes

ASJC Scopus Subject Areas

General Chemistry
Inorganic Chemistry

Keywords

Dehalogenation
Ionic liquid
Palladium complexes
Polybromofullerenes
Polyhalobenzenes

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10.1002/aoc.407

Cite this

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

abstract = "The novel, low-melting-point (19 °C) salt [N-pentylpyridinium]+ [closo-CB11H12]- (2) was synthesized in 93% yield and characterized by elemental analysis, IR spectroscopy, and 1H, 13C, and 11B 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 PdCl2(PPh3)2, PdCl2(dppe), and PdCl2(dppf). Complete debromination of C6Br6, 1,2,4,5-tetrabromobenzene, C60Br8, and C60Br24 was accomplished quite rapidly, whereas dechlorination of 1,2,4-trichlorobenzene proceeded more slowly, but with excellent products selectivity.",

keywords = "Dehalogenation, Ionic liquid, Palladium complexes, Polybromofullerenes, Polyhalobenzenes",

author = "Yinghuai Zhu and Chibun Ching and Keith Carpenter and Rong Xu and Selvasothi Selvaratnam and Hosmane, {Narayan S.} and Maguire, {John A.}",

year = "2003",

doi = "10.1002/aoc.407",

language = "English",

volume = "17",

pages = "346--350",

journal = "Applied Organometallic Chemistry",

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publisher = "John Wiley and Sons Ltd",

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T1 - Synthesis of the novel ionic liquid [N-pentylpyridinium]+ [closo-CB11H12]- and its usage as a reaction medium in catalytic dehalogenation of aromatic halides

AU - Zhu, Yinghuai

AU - Ching, Chibun

AU - Carpenter, Keith

AU - Xu, Rong

AU - Selvaratnam, Selvasothi

AU - Hosmane, Narayan S.

AU - Maguire, John A.

PY - 2003

Y1 - 2003

N2 - The novel, low-melting-point (19 °C) salt [N-pentylpyridinium]+ [closo-CB11H12]- (2) was synthesized in 93% yield and characterized by elemental analysis, IR spectroscopy, and 1H, 13C, and 11B 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 PdCl2(PPh3)2, PdCl2(dppe), and PdCl2(dppf). Complete debromination of C6Br6, 1,2,4,5-tetrabromobenzene, C60Br8, and C60Br24 was accomplished quite rapidly, whereas dechlorination of 1,2,4-trichlorobenzene proceeded more slowly, but with excellent products selectivity.

AB - The novel, low-melting-point (19 °C) salt [N-pentylpyridinium]+ [closo-CB11H12]- (2) was synthesized in 93% yield and characterized by elemental analysis, IR spectroscopy, and 1H, 13C, and 11B 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 PdCl2(PPh3)2, PdCl2(dppe), and PdCl2(dppf). Complete debromination of C6Br6, 1,2,4,5-tetrabromobenzene, C60Br8, and C60Br24 was accomplished quite rapidly, whereas dechlorination of 1,2,4-trichlorobenzene proceeded more slowly, but with excellent products selectivity.

KW - Dehalogenation

KW - Ionic liquid

KW - Palladium complexes

KW - Polybromofullerenes

KW - Polyhalobenzenes

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