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Molecules 2018, 23(7), 1696; https://doi.org/10.3390/molecules23071696

Indium-Mediated Allylation of Carbonyl Compounds in Ionic Liquids: Effect of Salts in Ionic Liquids

Life Science and Applied Chemistry, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan
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Academic Editors: Akio Baba and Makoto Yasuda
Received: 30 May 2018 / Revised: 9 July 2018 / Accepted: 10 July 2018 / Published: 11 July 2018
(This article belongs to the Special Issue Indium in Organic Synthesis)
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Abstract

The In-mediated allylation of carbonyl compounds can be performed in various types of solvents including ionic liquids. However, we have found that in [bmim][BF4] (where bmim = 1-butyl-3-methylimidazolium), the In-mediated coupling of crotyl bromide with benzaldehyde gives a complex mixture, and some additives, such as halides and amines, are crucial for the successful conversion to the corresponding γ-adduct. Instead, the addition of alcohols or water promotes the formation of the α-adduct. An asymmetric induction with up to 62% enantiomeric excess (ee) was observed employing cinchonidine as an additive in a binary solvent consisting of an ionic liquid and dichloromethane. View Full-Text
Keywords: indium; allylation; ionic liquids; carbonyl compounds; homoallylic alcohols indium; allylation; ionic liquids; carbonyl compounds; homoallylic alcohols
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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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Hirashita, T.; Takahashi, F.; Noda, T.; Takagi, Y.; Araki, S. Indium-Mediated Allylation of Carbonyl Compounds in Ionic Liquids: Effect of Salts in Ionic Liquids. Molecules 2018, 23, 1696.

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