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

Authors :
Foster D
Gao P
Zhang Z
Sipos G
Sobolev AN
Nealon G
Falivene L
Cavallo L
Dorta R
Source :
Chemical science [Chem Sci] 2021 Feb 01; Vol. 12 (10), pp. 3751-3767. Date of Electronic Publication: 2021 Feb 01.
Publication Year :
2021

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.<br />Competing Interests: There are no conflicts to declare.<br /> (This journal is © The Royal Society of Chemistry.)

Details

Language :
English
ISSN :
2041-6520
Volume :
12
Issue :
10
Database :
MEDLINE
Journal :
Chemical science
Publication Type :
Academic Journal
Accession number :
34163649
Full Text :
https://doi.org/10.1039/d0sc05884j