Indium(III) as π-acid Catalyst for the Electrophilic Activation of Carbon–Carbon Unsaturated Systems
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Indium(III) as π-acid Catalyst for the Electrophilic Activation of Carbon–Carbon Unsaturated SystemsDate
2018-07-25Citation
Sestelo, J. P., Sarandeses, L. A., Martínez, M. M., & Alonso-Marañón, L. (2018). Indium(III) as π-acid catalyst for the electrophilic activation of carbon–carbon unsaturated systems. Organic & Biomolecular Chemistry, 16(32), 5733-5747. https://doi.org/10.1039/C8OB01426D
Abstract
[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.
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© The Royal Society of Chemistry 2018
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1477-0539