An efficient and green method for regio- and chemo-selective Friedel–Crafts acylations using a deep eutectic mixture ([CholineCl][ZnCl2]3)

Tran Phuong Hoang, Hai Truong Nguyen, Poul Erik Hansen, Thach Ngoc Le

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

Resumé

[CholineCl][ZnCl2]3, a deep eutectic solvent between choline chloride and ZnCl2, has been used as a dual function catalyst and green solvent for the Friedel–Crafts acylation of aromatic compounds instead of using the moisture-sensitive Lewis acids and volatile organic solvents. The reactions are performed with high yields under microwave irradiation with short reaction times for the synthesis of ketones. Interestingly, indole derivatives are regioselectively acylated in the 3-position under mild conditions with high yields without NH protection. Three new ketone products are synthesized. [CholineCl][ZnCl2]3 is easily synthesized from choline chloride and zinc chloride at a low cost, with easy purification and environmentally benign compounds. [CholineCl][ZnCl2]3 can be reused up to five times without loss of catalytic activity, making it ideal in industrial processes.
OriginalsprogEngelsk
TidsskriftRSC Advances
Vol/bind2016
Udgave nummer43
Sider (fra-til)37031-37038
Antal sider8
ISSN2046-2069
StatusUdgivet - 1 aug. 2016

Emneord

  • Deep eutectic solvents
  • ionic liquids
  • Friede-Crafts acylation
  • choline chloride
  • zinc chloride

Citer dette

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title = "An efficient and green method for regio- and chemo-selective Friedel–Crafts acylations using a deep eutectic mixture ([CholineCl][ZnCl2]3)",
abstract = "[CholineCl][ZnCl2]3, a deep eutectic solvent between choline chloride and ZnCl2, has been used as a dual function catalyst and green solvent for the Friedel–Crafts acylation of aromatic compounds instead of using the moisture-sensitive Lewis acids and volatile organic solvents. The reactions are performed with high yields under microwave irradiation with short reaction times for the synthesis of ketones. Interestingly, indole derivatives are regioselectively acylated in the 3-position under mild conditions with high yields without NH protection. Three new ketone products are synthesized. [CholineCl][ZnCl2]3 is easily synthesized from choline chloride and zinc chloride at a low cost, with easy purification and environmentally benign compounds. [CholineCl][ZnCl2]3 can be reused up to five times without loss of catalytic activity, making it ideal in industrial processes.",
keywords = "Deep eutectic solvents, ionic liquids, Friede-Crafts acylation, choline chloride, zinc chloride, deep eutedtic solvents, micorwave, Friede-Crafts acylation",
author = "Hoang, {Tran Phuong} and Nguyen, {Hai Truong} and Hansen, {Poul Erik} and Le, {Thach Ngoc}",
year = "2016",
month = "8",
day = "1",
language = "English",
volume = "2016",
pages = "37031--37038",
journal = "RSC Advances",
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An efficient and green method for regio- and chemo-selective Friedel–Crafts acylations using a deep eutectic mixture ([CholineCl][ZnCl2]3). / Hoang, Tran Phuong; Nguyen, Hai Truong ; Hansen, Poul Erik; Le, Thach Ngoc.

I: RSC Advances, Bind 2016, Nr. 43, 01.08.2016, s. 37031-37038.

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

TY - JOUR

T1 - An efficient and green method for regio- and chemo-selective Friedel–Crafts acylations using a deep eutectic mixture ([CholineCl][ZnCl2]3)

AU - Hoang, Tran Phuong

AU - Nguyen, Hai Truong

AU - Hansen, Poul Erik

AU - Le, Thach Ngoc

PY - 2016/8/1

Y1 - 2016/8/1

N2 - [CholineCl][ZnCl2]3, a deep eutectic solvent between choline chloride and ZnCl2, has been used as a dual function catalyst and green solvent for the Friedel–Crafts acylation of aromatic compounds instead of using the moisture-sensitive Lewis acids and volatile organic solvents. The reactions are performed with high yields under microwave irradiation with short reaction times for the synthesis of ketones. Interestingly, indole derivatives are regioselectively acylated in the 3-position under mild conditions with high yields without NH protection. Three new ketone products are synthesized. [CholineCl][ZnCl2]3 is easily synthesized from choline chloride and zinc chloride at a low cost, with easy purification and environmentally benign compounds. [CholineCl][ZnCl2]3 can be reused up to five times without loss of catalytic activity, making it ideal in industrial processes.

AB - [CholineCl][ZnCl2]3, a deep eutectic solvent between choline chloride and ZnCl2, has been used as a dual function catalyst and green solvent for the Friedel–Crafts acylation of aromatic compounds instead of using the moisture-sensitive Lewis acids and volatile organic solvents. The reactions are performed with high yields under microwave irradiation with short reaction times for the synthesis of ketones. Interestingly, indole derivatives are regioselectively acylated in the 3-position under mild conditions with high yields without NH protection. Three new ketone products are synthesized. [CholineCl][ZnCl2]3 is easily synthesized from choline chloride and zinc chloride at a low cost, with easy purification and environmentally benign compounds. [CholineCl][ZnCl2]3 can be reused up to five times without loss of catalytic activity, making it ideal in industrial processes.

KW - Deep eutectic solvents

KW - ionic liquids

KW - Friede-Crafts acylation

KW - choline chloride

KW - zinc chloride

KW - deep eutedtic solvents

KW - micorwave

KW - Friede-Crafts acylation

M3 - Journal article

VL - 2016

SP - 37031

EP - 37038

JO - RSC Advances

JF - RSC Advances

SN - 2046-2069

IS - 43

ER -