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Issue 32, 2018
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Indium(iii) as π-acid catalyst for the electrophilic activation of carbon–carbon unsaturated systems

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Abstract

This review focuses on the utilization of indium(III) as π-acid for the activation of C–C unsaturated bonds in organic synthesis. In addition to its well-known σ-coordination with carbonyl derivatives, indium(III) undergoes efficient π-coordination with unsaturated systems to trigger nucleophilic addition. Accordingly, indium(III) halides and salts (InX3, X = Cl, Br, I, OTf, ONf, NTf2) have been reported as useful catalysts for a broad range of carbon–carbon and carbon–heteroatom bond formation reactions, including hydrofunctionalization (hydroarylation, hydroamination, hydroalkoxylation, and hydrothiolation), enyne cycloisomerization, and related reactions. In these reactions the counterion has a significant effect on the catalytic activity, and the development of novel In(III) complexes and the generation of highly electrophilic cationic indium(III) species has increased its synthetic applications as a π-acid catalyst.

Graphical abstract: Indium(iii) as π-acid catalyst for the electrophilic activation of carbon–carbon unsaturated systems

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Article information


Submitted
16 Jun 2018
Accepted
25 Jul 2018
First published
25 Jul 2018

Org. Biomol. Chem., 2018,16, 5733-5747
Article type
Review Article

Indium(III) as π-acid catalyst for the electrophilic activation of carbon–carbon unsaturated systems

J. Pérez Sestelo, L. A. Sarandeses, M. M. Martínez and L. Alonso-Marañón, Org. Biomol. Chem., 2018, 16, 5733
DOI: 10.1039/C8OB01426D

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