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

Font Molíns, MarcCendón Mariño, BorjaSeoane Fernández, AndrésMascareñas Cid, José LuisGulías Costa, Moisés2018-06-072018-11-042018-05-04Font, 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.2018028301521-3757http://hdl.handle.net/10347/16765A 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 shifteng© 2018 WILEY‐VCH Verlag GmbH & Co. KGaA, WeinheimC-H activationAnnulationRhodiumCatalysisRhodium(III)‐Catalyzed Annulation of 2‐Alkenylanilides with Alkynes via C‐H Activation: a Direct Access to 2‐substituted Indolinesjournal article10.1002/anie.201802830open access