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Rhodium(III)‐Catalyzed Annulation of 2‐Alkenyl Anilides with Alkynes through C−H Activation: Direct Access to 2‐Substituted Indolines
Author(s) -
Font Marc,
Cendón Borja,
Seoane Andrés,
Mascareñas José Luis,
Gulías Moisés
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201802830
Subject(s) - annulation , rhodium , amination , chemistry , alkyne , allylic rearrangement , catalysis , ligand (biochemistry) , cyclopentadienyl complex , medicinal chemistry , stereochemistry , organic chemistry , receptor , biochemistry
A Rh III complex featuring an electron‐deficient η 5 ‐cyclopentadienyl ligand catalyzed an unusual annulation between alkynes and 2‐alkenyl anilides 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 an unusual rhodium migration with a concomitant 1,5‐H shift.