Issue 32, 2018

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

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

Article information

Article type
Review Article
Submitted
16 jun 2018
Accepted
25 jul 2018
First published
25 jul 2018

Org. Biomol. Chem., 2018,16, 5733-5747

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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