Developing NHC-Iridium Catalysts for the Highly Efficient Enantioselective Intramolecular Hydroamination Reaction

Pengchao Gao, Gellert Sipos, Daven Foster, Reto Dorta

Research output: Contribution to journalArticle

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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 pyrrolidines, which are accessed with excellent optical purity. Enantiomerically enriched piperidines and indolines are also produced, and various functional groups are tolerated with this LTM system. A reaction mechanism is proposed, and a major deactivation pathway of these catalysts is presented and discussed.

Original languageEnglish
Pages (from-to)6060-6064
Number of pages5
JournalACS Catalysis
Volume7
Issue number9
DOIs
Publication statusPublished - Sep 2017

Cite this

Gao, Pengchao ; Sipos, Gellert ; Foster, Daven ; Dorta, Reto. / Developing NHC-Iridium Catalysts for the Highly Efficient Enantioselective Intramolecular Hydroamination Reaction. In: ACS Catalysis. 2017 ; Vol. 7, No. 9. pp. 6060-6064.
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Developing NHC-Iridium Catalysts for the Highly Efficient Enantioselective Intramolecular Hydroamination Reaction. / Gao, Pengchao; Sipos, Gellert; Foster, Daven; Dorta, Reto.

In: ACS Catalysis, Vol. 7, No. 9, 09.2017, p. 6060-6064.

Research output: Contribution to journalArticle

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T1 - Developing NHC-Iridium Catalysts for the Highly Efficient Enantioselective Intramolecular Hydroamination Reaction

AU - Gao, Pengchao

AU - Sipos, Gellert

AU - Foster, Daven

AU - Dorta, Reto

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AB - 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 pyrrolidines, which are accessed with excellent optical purity. Enantiomerically enriched piperidines and indolines are also produced, and various functional groups are tolerated with this LTM system. A reaction mechanism is proposed, and a major deactivation pathway of these catalysts is presented and discussed.

KW - chiral NHC

KW - iridium

KW - catalysis

KW - hydroamination

KW - N-heterocycles

KW - ASYMMETRIC HYDROAMINATION

KW - UNACTIVATED ALKENES

KW - ALPHA-ARYLATION

KW - COMPLEXES

KW - AMINES

KW - AMINOALKENES

KW - CYCLIZATION

KW - AMIDES

KW - HYDROGENATION

KW - ARYLAMINES

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