Rhodium(III)‐Catalyzed Annulation of 2‐Alkenylanilides with Alkynes via C‐H Activation: a Direct Access to 2‐substituted Indolines

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URI: http://hdl.handle.net/10347/16765
ISSN: 1521-3757
DOI: 10.1002/anie.201802830

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2018-05-04

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Wiley
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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

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C-H activation| Annulation| Rhodium| Catalysis

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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

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This work has received financial support from Spanish grants (SAF2016-76689-R and CTQ2016-77047-P), the Xunta de Galicia (ED431C 2017/19, 2015-CP082 and Centro Singular de Investigación de Galicia accreditation 2016-2019, ED431G/09) the European Regional Development Fund (ERDF), and the European Research Council (Advanced Grant No. 340055). The orfeo-cinqa network CTQ2016-81797-REDC is also kindly acknowledged

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© 2018 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim

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Química Orgánica