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Iridium Catalyzed Synthesis of Tetrahydro-1H-Indoles by Dehydrogenative Condensation

Inorganic Chemistry II—Catalyst Design, University of Bayreuth, D-95440 Bayreuth, Germany
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Inorganics 2019, 7(8), 97; https://doi.org/10.3390/inorganics7080097
Received: 27 June 2019 / Revised: 1 August 2019 / Accepted: 2 August 2019 / Published: 6 August 2019
(This article belongs to the Special Issue Iridium Complexes)
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Abstract

Novel synthetic routes to the commonly encountered indole motif are highly sought after. Tetrahydro-1H-indoles were synthesized for the first time from secondary alcohols and 2-aminocyclohexanol in the presence of a well-established iridium catalyst using a modified synthetic procedure recently developed for the synthesis of hydrocarbazoles. The catalyst is stabilized by an inexpensive and easy-to-synthesize triazine based PN5P pincer ligand. The reaction proceeds through acceptorless dehydrogenative condensation (ADC) and yields the title compound, dihydrogen, and water and can thus be classified as sustainable synthesis. Overall, five examples, three of which were previously unknown compounds, were prepared. The propitious isolated yields and the mild reaction conditions show the synthetic value of this approach. These tetrahydroindoles can be quantitatively dehydrogenated over a heterogeneous Pd catalyst to yield the corresponding indoles. View Full-Text
Keywords: catalysis; dehydrogenation; indoles; iridium; sustainable synthesis catalysis; dehydrogenation; indoles; iridium; sustainable synthesis
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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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Forberg, D.; Kallmeier, F.; Kempe, R. Iridium Catalyzed Synthesis of Tetrahydro-1H-Indoles by Dehydrogenative Condensation. Inorganics 2019, 7, 97.

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