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Molecules 2015, 20(10), 19605-19619; doi:10.3390/molecules201019605

A Simple, Effective, Green Method for the Regioselective 3-Acylation of Unprotected Indoles

1
Department of Organic Chemistry, Faculty of Chemistry, University of Science, Vietnam National University, Ho Chi Minh City 70000, Vietnam
2
Department of Science, Systems and Models, Roskilde University, POB 260, Roskilde DK-4000, Denmark
*
Author to whom correspondence should be addressed.
Academic Editor: Jason P. Hallett
Received: 5 October 2015 / Revised: 22 October 2015 / Accepted: 22 October 2015 / Published: 27 October 2015
(This article belongs to the Special Issue Ionic Liquids in Organic Synthesis)
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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. View Full-Text
Keywords: Friedel-Crafts acylation; indole derivatives; ionic liquids; metal triflate; microwave irradiation Friedel-Crafts acylation; indole derivatives; ionic liquids; metal triflate; microwave irradiation
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Tran, P.H.; Tran, H.N.; Hansen, P.E.; Do, M.H.N.; Le, T.N. A Simple, Effective, Green Method for the Regioselective 3-Acylation of Unprotected Indoles. Molecules 2015, 20, 19605-19619.

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