Rhodium(III)‐Catalyzed Annulation of 2‐Alkenylanilides with Alkynes via C‐H Activation: a Direct Access to 2‐substituted Indolines
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| Title: | Rhodium(III)‐Catalyzed Annulation of 2‐Alkenylanilides with Alkynes via C‐H Activation: a Direct Access to 2‐substituted Indolines |
| Author: | Font Molíns, Marc Cendón Mariño, Borja Seoane Fernández, Andrés Mascareñas Cid, José Luis Gulías Costa, Moisés |
| Affiliation: | Universidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares Universidade de Santiago de Compostela. Departamento de Química Orgánica |
| Subject: | C-H activation | Annulation | Rhodium | Catalysis | |
| Date of Issue: | 2018-05-04 |
| Publisher: | Wiley |
| Citation: | Font, M., Cendón, B., Seoane, A., Mascareñas, J., & Gulías, M. (2018). Rhodium(III)-Catalyzed Annulation of 2-Alkenyl Anilides with Alkynes through C−H Activation: Direct Access to 2-Substituted Indolines. Angewandte Chemie International Edition. doi: 10.1002/anie.201802830 |
| Abstract: | A Rh(III) complex featuring an electron‐deficient η5‐cyclopentadienyl ligand catalyzes an unusual annulation between alkynes and 2‐alkenylanilides, to form synthetically appealing 2‐substituted indolines. Formally, the process can be viewed as an allylic amination with concomitant hydrocarbonation of the alkyne. Mechanistic experiments indicate that this transformation involves a peculiar Rhodium migration with a concomitant 1,5‐H shift |
| Publisher version: | https://doi.org/10.1002/anie.201802830 |
| URI: | http://hdl.handle.net/10347/16765 |
| DOI: | 10.1002/anie.201802830 |
| ISSN: | 1521-3757 |
| Rights: | © 2018 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim |
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