The [IrCl(Diphosphine)]<sub>2</sub>/Fluoride System. Developing Catalytic Asymmetric Olefin Hydroamination

Dorta, Romano; Egli, Patrick; Zürcher, and Fabio; Togni, Antonio

doi:10.1021/ja972594k

Cited by 334 publications

(188 citation statements)

References 24 publications

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“…[101] Addition of aniline to a slurry of norbornene and [Ir( Recently, several examples of enantioselective, iridium-catalyzed hydroamination reactions of strained bicyclic alkenes were reported, along with evidence that the reactions occur by migratory insertion of the alkene into an IrÀN bond. [102][103][104][105] More recently, Hartwig and co-workers reported the transfer of an amido group to alkenes and vinylarenes from an isolated rhodium amido complex. [106] A series of triethylphosphine-ligated rhodium amido complexes react with vinylarenes at 60 8C to from the corresponding N-aryl imine and a dimeric hydridorhodium amide complex (Scheme 23).…”

Section: Reactions Of Metal Amido Complexes With Alkenes For Which DImentioning

confidence: 99%

Migratory Insertion of Alkenes into Metal–Oxygen and Metal–Nitrogen Bonds

Hanley

Hartwig

2013

Angew Chem Int Ed

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The insertion of an unsaturated ligand into a MC or MH bond proceeds through migratory insertion, a fundamental organometallic reaction. Recent literature documents evidence of the migratory insertion of alkenes into an MO and MN bonds for alkene alkoxylation and alkene amination reactions, respectively. Herein we provide an overview of the literature and a perspective on how these recent experiments relate to classic experiments on CO and CN bond formation with alkene complexes of the late transition metals.

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Section: Reactions Of Metal Amido Complexes With Alkenes For Which DImentioning

confidence: 99%

Migratory Insertion of Alkenes into Metal–Oxygen and Metal–Nitrogen Bonds

Hanley

Hartwig

2013

Angew Chem Int Ed

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“…Asymmetric 65 hydroamination reactions of unactivated alkenes have been limited almost exclusively to intramolecular cyclisation of aminoalkenes, 1,14 with some limited intermolecular examples involving the addition of anilines to norbornene and styrene, catalysed by iridium 34 and palladium, 35 respectively.…”

Section: Introduction Scheme 1 Hydroamination Reactionsmentioning

confidence: 99%

Hydroamination reactions by metal triflates: Brønsted acid vs. metal catalysis?

2010

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Catalytic hydroamination reactions involving the addition of carboxamide, carbamates and sulfonamides to unactivated C=C bonds are briefly reviewed. Development in this field of catalytic research is briefly charted, followed by a discussion of possible mechanisms, including arguments to support the operation of both metal and Brønsted acid catalysis in these systems. Future developments in the area are summarised.

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“…The number of parameters is 455. Flack c parameter shows À 0.018 (7), and the absolute configuration of the binap ligand is R. GOF values are 1.153 for I b 2.0s(I) and 1.146 for all data. The maximum shift to esd ratio in the last full-matrix least-squares cycle was 0.000.…”

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confidence: 90%

Facile Oxidative Addition of O−H Bonds of Methanol and Water to IrI Complexes Having Peraryldiphosphane Ligands

Tani

Iseki

Yamagata

1998

Angewandte Chemie International Edition

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A new piece in the puzzle. Hydrido(alkoxo) complexes of late transition metals have often been postulated as intermediates or transition states in the catalytic hydrogenation of carbonyl compounds and catalytic hydrogen transfer reactions. Here the facile oxidative addition of the O-H bonds of alcohol and water to iridium(I) complexes of peraryldiphosphanes [Eq. (a)] is reported and the resulting complexes are described. R=H, Me.

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The [IrCl(Diphosphine)]₂/Fluoride System. Developing Catalytic Asymmetric Olefin Hydroamination

Cited by 334 publications

References 24 publications

Migratory Insertion of Alkenes into Metal–Oxygen and Metal–Nitrogen Bonds

Migratory Insertion of Alkenes into Metal–Oxygen and Metal–Nitrogen Bonds

Hydroamination reactions by metal triflates: Brønsted acid vs. metal catalysis?

Facile Oxidative Addition of O−H Bonds of Methanol and Water to IrI Complexes Having Peraryldiphosphane Ligands

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The [IrCl(Diphosphine)]2/Fluoride System. Developing Catalytic Asymmetric Olefin Hydroamination

Cited by 334 publications

References 24 publications

Migratory Insertion of Alkenes into Metal–Oxygen and Metal–Nitrogen Bonds

Migratory Insertion of Alkenes into Metal–Oxygen and Metal–Nitrogen Bonds

Hydroamination reactions by metal triflates: Brønsted acid vs. metal catalysis?

Facile Oxidative Addition of O−H Bonds of Methanol and Water to IrI Complexes Having Peraryldiphosphane Ligands

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The [IrCl(Diphosphine)]₂/Fluoride System. Developing Catalytic Asymmetric Olefin Hydroamination