Unusual base dependent enantioselectivity in a transfer hydrogenation using axially chiral Ir(III)-catalysts

Furegati, Markus; Rippert, Andreas Johannes

doi:10.1016/j.tetasy.2005.11.002

Cited by 20 publications

(14 citation statements)

References 30 publications

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“…A new bidentate monosulfonated diamine with an axially chiral biaryl backbone in combination with [Cp*IrCl 2 ] 2 was recently reported for the ATH of ketones in isopropanol [102], affording moderate ee's.…”

Section: Hydrogen Transfer Reactionsmentioning

confidence: 99%

Half-sandwich iridium complexes—Synthesis and applications in catalysis

Liu

Iggo

et al. 2008

Coordination Chemistry Reviews

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Section: Hydrogen Transfer Reactionsmentioning

confidence: 99%

Half-sandwich iridium complexes—Synthesis and applications in catalysis

Liu

Iggo

et al. 2008

Coordination Chemistry Reviews

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“…6,7 Crabtree et al have utilised an Ir(III) hydride complex to achieve alkyne insertion into a Ir-H, and also catalyse the intramolecular hydroamination and hydroalkoxylation of alkynes. Odile.Eisenstein@univ-montp2.fr of amines with alcohols 11, 12 and the transfer hydrogenation of ketones 13 and quinolines. 14 N-vinyl indoles have been used as monomers in the production of poly(N-vinyl indoles) which found application in the production of photorefractive materials.…”

Section: Introductionmentioning

confidence: 99%

The mechanism of N-vinylindole formation via tandem imine formation and cycloisomerisation of o-ethynylanilines

et al. 2009

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The reaction of 2-(2-phenylethynyl)aniline with acetone in presence of [IrCp*Cl(2)](2) has previously been found to yield a vinyl indole derivative and not the indole expected to form following a hydroamination reaction. Experimental data, including labelling studies, isolation and solid state structure determination of a reaction intermediate together with DFT calculations were used to develop a mechanism for the formation of the vinyl indole. In the mechanism proposed, acetone plays a significant role in several steps of the reaction path, participating in the fragmentation of the dinuclear Ir complex and the formation of the reactive form of the catalyst as well as blocking the formation of the expected hydroamination product by coordination to the Ir catalyst. Coordinated acetone reacts with the aniline to form an imine derivative, which yields the final product following proton transfer promoted by acetone. The proposed mechanism is in good agreement with the experimental data.

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“…Recent work by Crabtree et al has utilised an Ir III hydride complex to catalyse the intramolecular hydroamination and hydroalkoxylation of alkynes 16. [Cp*IrCl 2 ] 2 is effective as a catalyst for the hydroborylation of styryl sulfonamides,17 the N ‐alkylation of amines with alcohols18 and also the transfer hydrogenation of ketones19 and quinolines 20. Rh III complexes are known to be effective in catalysing carbon–carbon bond formation,21 and [Cp*RhCl 2 ] 2 has been shown to effect transfer dehydrochlorination of aryl chlorides 22…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Cp* Iridium and Rhodium Complexes Containing Bidentate sp²‐N‐Donor Ligands and Counter‐Anions [Cp*MCl₃]^–

2006

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Unusual base dependent enantioselectivity in a transfer hydrogenation using axially chiral Ir(III)-catalysts

Cited by 20 publications

References 30 publications

Half-sandwich iridium complexes—Synthesis and applications in catalysis

Half-sandwich iridium complexes—Synthesis and applications in catalysis

The mechanism of N-vinylindole formation via tandem imine formation and cycloisomerisation of o-ethynylanilines

Synthesis of Cp* Iridium and Rhodium Complexes Containing Bidentate sp²‐N‐Donor Ligands and Counter‐Anions [Cp*MCl₃]^–

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Unusual base dependent enantioselectivity in a transfer hydrogenation using axially chiral Ir(III)-catalysts

Cited by 20 publications

References 30 publications

Half-sandwich iridium complexes—Synthesis and applications in catalysis

Half-sandwich iridium complexes—Synthesis and applications in catalysis

The mechanism of N-vinylindole formation via tandem imine formation and cycloisomerisation of o-ethynylanilines

Synthesis of Cp* Iridium and Rhodium Complexes Containing Bidentate sp2‐N‐Donor Ligands and Counter‐Anions [Cp*MCl3]–

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Synthesis of Cp* Iridium and Rhodium Complexes Containing Bidentate sp²‐N‐Donor Ligands and Counter‐Anions [Cp*MCl₃]^–