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

Pengchao Gao; Gellert Sipos; Daven Foster; Reto Dorta

doi:10.1021/acscatal.7b02508

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

Pengchao Gao, Gellert Sipos, Daven Foster, Reto Dorta

School of Molecular Sciences

Research output: Contribution to journal › Article › peer-review

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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 language	English
Pages (from-to)	6060-6064
Number of pages	5
Journal	ACS Catalysis
Volume	7
Issue number	9
DOIs	https://doi.org/10.1021/acscatal.7b02508
Publication status	Published - Sept 2017

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10.1021/acscatal.7b02508

Pengchao et al 2017 Developing NHC-Iridium Catalysts for the Highly Efficient Enantioselective Intramolecular Hydroamination ReactionAccepted author manuscript, 782 KB

New Chiral Metal Catalysts; Going Beyond the State of the Art
Dorta, R. (Investigator 01)
ARC Australian Research Council
1/01/13 → 31/12/18
Project: Research

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title = "Developing NHC-Iridium Catalysts for the Highly Efficient Enantioselective Intramolecular Hydroamination Reaction",

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.",

keywords = "chiral NHC, iridium, catalysis, hydroamination, N-heterocycles, ASYMMETRIC HYDROAMINATION, UNACTIVATED ALKENES, ALPHA-ARYLATION, COMPLEXES, AMINES, AMINOALKENES, CYCLIZATION, AMIDES, HYDROGENATION, ARYLAMINES",

author = "Pengchao Gao and Gellert Sipos and Daven Foster and Reto Dorta",

year = "2017",

month = sep,

doi = "10.1021/acscatal.7b02508",

language = "English",

volume = "7",

pages = "6060--6064",

journal = "ACS Catalysis",

issn = "2155-5435",

publisher = "American Chemical Society",

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TY - JOUR

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

PY - 2017/9

Y1 - 2017/9

N2 - 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.

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

U2 - 10.1021/acscatal.7b02508

DO - 10.1021/acscatal.7b02508

M3 - Article

SN - 2155-5435

VL - 7

SP - 6060

EP - 6064

JO - ACS Catalysis

JF - ACS Catalysis

IS - 9

ER -

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

Abstract

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New Chiral Metal Catalysts; Going Beyond the State of the Art

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