Premium
Intermolecular, Branch‐Selective, and Redox‐Neutral Cp*Ir III ‐Catalyzed Allylic C−H Amidation
Author(s) -
Knecht Tobias,
Mondal Shobhan,
Ye JianHeng,
Das Mowpriya,
Glorius Frank
Publication year - 2019
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.201901733
Subject(s) - allylic rearrangement , intermolecular force , chemistry , catalysis , redox , nucleophile , nucleophilic addition , medicinal chemistry , stereochemistry , molecule , organic chemistry
Herein, we report the redox‐neutral, intermolecular, and highly branch‐selective amidation of allylic C−H bonds enabled by Cp*Ir III catalysis. A variety of readily available carboxylic acids were converted into the corresponding dioxazolones and efficiently coupled with terminal and internal olefins in high yields and selectivities. Mechanistic investigations support the formation of a nucleophilic Ir III –allyl intermediate rather than the direct insertion of an Ir–nitrenoid species into the allylic C−H bond.