Design, scope and mechanism of highly active and selective chiral NHC-iridium catalysts for the intramolecular hydroamination of a variety of unactivated aminoalkenes

Daven Foster, Pengchao Gao, Ziyun Zhang, Gellért Sipos, Alexandre N. Sobolev, Gareth Nealon, Laura Falivene, Luigi Cavallo, Reto Dorta

Research output: Contribution to journalArticle

Abstract

Chiral, cationic NHC-iridium complexes are introduced as catalysts for the intramolecular hydroamination reaction of unactivated aminoalkenes. The catalysts show high activity in the construction of a range of 5- and 6-membered N-heterocycles, which are accessed in excellent optical purity, with various functional groups being tolerated with this system. A major deactivation pathway is presented and eliminated by using alternative reaction conditions. A detailed experimental and computational study on the reaction mechanism is performed providing valuable insights into the mode of action of the catalytic system and pointing to future modifications to be made for this catalytic platform.

Original languageEnglish
Pages (from-to)3751-3767
Number of pages17
JournalChemical Science
Volume12
Issue number10
DOIs
Publication statusPublished - 14 Mar 2021

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