A simple, effective, green method for regioselective 3-acylation of unprotected indoles

Phuong Huong Tran, Hai N. Tran, Poul Erik Hansen, Mai Hoang Ngoc Do, Thach N Le

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › peer review

Resumé

A fast and green method is developed for regioselective acylation of indoles in the 3-position without the need for protection of the NH position. The method is based on Friedel-Crafts acylation using acid anhydrides. The method has been optimized, and Y(OTf)3 in catalytic amounts is found to be the best catalyst together with the commercially available ionic liquid [BMI]BF4 (1-butyl-3-methylimidazolium tetrafluoro-borate) as solvent. The reaction is completed in a very short time using monomode microwave irradiation. The catalyst can be reused up to four times without significant loss of activity. A range of substituted indoles are investigated as substrates, and thirteen new compounds have been synthesized
OriginalsprogEngelsk
TidsskriftMolecules
Vol/bind20
Udgave nummer10
Sider (fra-til)19605-19619
Antal sider15
ISSN1420-3049
DOI
StatusUdgivet - 2015

Emneord

  • indoles
  • Friedel-Crafts
  • acylation
  • green chemistry
  • ionic liquids
  • ytterbium triflate
  • microwave

Citer dette

Tran, Phuong Huong ; Tran, Hai N. ; Hansen, Poul Erik ; Do, Mai Hoang Ngoc ; Le, Thach N. / A simple, effective, green method for regioselective 3-acylation of unprotected indoles. I: Molecules. 2015 ; Bind 20, Nr. 10. s. 19605-19619.
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title = "A simple, effective, green method for regioselective 3-acylation of unprotected indoles",
abstract = "A fast and green method is developed for regioselective acylation of indoles in the 3-position without the need for protection of the NH position. The method is based on Friedel-Crafts acylation using acid anhydrides. The method has been optimized, and Y(OTf)3 in catalytic amounts is found to be the best catalyst together with the commercially available ionic liquid [BMI]BF4 (1-butyl-3-methylimidazolium tetrafluoro-borate) as solvent. The reaction is completed in a very short time using monomode microwave irradiation. The catalyst can be reused up to four times without significant loss of activity. A range of substituted indoles are investigated as substrates, and thirteen new compounds have been synthesized",
keywords = "indoles, Friedel-Crafts, acylation, green chemistry, ionic liquids, ytterbium triflate, microwave, Friedel-Crafts, Ytterbium, Ionic Liquid, green chemistry, unprotected indoles, acylation",
author = "Tran, {Phuong Huong} and Tran, {Hai N.} and Hansen, {Poul Erik} and Do, {Mai Hoang Ngoc} and Le, {Thach N}",
year = "2015",
doi = "10.3390/molecules201019605",
language = "English",
volume = "20",
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journal = "Molecules",
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Tran, PH, Tran, HN, Hansen, PE, Do, MHN & Le, TN 2015, 'A simple, effective, green method for regioselective 3-acylation of unprotected indoles', Molecules, bind 20, nr. 10, s. 19605-19619. https://doi.org/10.3390/molecules201019605

A simple, effective, green method for regioselective 3-acylation of unprotected indoles. / Tran, Phuong Huong; Tran, Hai N. ; Hansen, Poul Erik; Do, Mai Hoang Ngoc ; Le, Thach N.

I: Molecules, Bind 20, Nr. 10, 2015, s. 19605-19619.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › peer review

TY - JOUR

T1 - A simple, effective, green method for regioselective 3-acylation of unprotected indoles

AU - Tran, Phuong Huong

AU - Tran, Hai N.

AU - Hansen, Poul Erik

AU - Do, Mai Hoang Ngoc

AU - Le, Thach N

PY - 2015

Y1 - 2015

N2 - A fast and green method is developed for regioselective acylation of indoles in the 3-position without the need for protection of the NH position. The method is based on Friedel-Crafts acylation using acid anhydrides. The method has been optimized, and Y(OTf)3 in catalytic amounts is found to be the best catalyst together with the commercially available ionic liquid [BMI]BF4 (1-butyl-3-methylimidazolium tetrafluoro-borate) as solvent. The reaction is completed in a very short time using monomode microwave irradiation. The catalyst can be reused up to four times without significant loss of activity. A range of substituted indoles are investigated as substrates, and thirteen new compounds have been synthesized

AB - A fast and green method is developed for regioselective acylation of indoles in the 3-position without the need for protection of the NH position. The method is based on Friedel-Crafts acylation using acid anhydrides. The method has been optimized, and Y(OTf)3 in catalytic amounts is found to be the best catalyst together with the commercially available ionic liquid [BMI]BF4 (1-butyl-3-methylimidazolium tetrafluoro-borate) as solvent. The reaction is completed in a very short time using monomode microwave irradiation. The catalyst can be reused up to four times without significant loss of activity. A range of substituted indoles are investigated as substrates, and thirteen new compounds have been synthesized

KW - indoles

KW - Friedel-Crafts

KW - acylation

KW - green chemistry

KW - ionic liquids

KW - ytterbium triflate

KW - microwave

KW - Friedel-Crafts

KW - Ytterbium

KW - Ionic Liquid

KW - green chemistry

KW - unprotected indoles

KW - acylation

U2 - 10.3390/molecules201019605

DO - 10.3390/molecules201019605

M3 - Journal article

VL - 20

SP - 19605

EP - 19619

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 10

ER -

Tran PH, Tran HN, Hansen PE, Do MHN, Le TN. A simple, effective, green method for regioselective 3-acylation of unprotected indoles. Molecules. 2015;20(10):19605-19619. https://doi.org/10.3390/molecules201019605

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