New P,N-ferrocenyl ligands for rhodium-catalyzed hydroboration and palladium-catalyzed allylic alkylation

Kloetzing, Ralf J.; Lotz, Matthias; Knöchel, Paul

doi:10.1016/s0957-4166(02)00827-3

Cited by 50 publications

(24 citation statements)

References 26 publications

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“…In the presence of N,N-dimethyl-1- [2-(diphenylphosphino)ferrocenyl]ethylamine (13, ppfa) as a ligand, a C 2 -symmetrical binaphthalene was obtained in very good enantioselectivity (up to 85% ee) via an enantioselective Suzuki cross-coupling [95,96]. [99].…”

Section: Miscellaneous Reactionsmentioning

confidence: 99%

Ferrocene-derived P,N ligands: synthesis and application in enantioselective catalysis

Noël¹,

Eycken²

2013

Green Processing and Synthesis

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Due to their unique steric and electronic properties, air-stability and modular structure, chiral hybrid P,N-ferrocenyl ligands play a prominent role in the field of asymmetric catalysis. This report aims to give a concise introduction to the syntheses of chiral hybrid P,N-ferrocenyl ligands and presents an overview of their application in enantioselective catalysis. This review is of special interest to chemists working on ligand design and asymmetric catalysis, as well as to the broader organic and inorganic community.

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Section: Miscellaneous Reactionsmentioning

confidence: 99%

Ferrocene-derived P,N ligands: synthesis and application in enantioselective catalysis

Noël¹,

Eycken²

2013

Green Processing and Synthesis

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“…These ligands were tested in the rhodium-catalysed asymmetric hydroboration-oxidation of styrene (38), and representative results are shown in Table 14. [134] Ligands 109 -111 with a pyrimidyl group showed excellent regioselectivity but only moderate conversion and enantioselectivity, entry 1. In contrast, rhodium complexes of ligands 115 -117 bearing a quinolyl group were highly efficient catalysts, inducing excellent enantioselectivity but at the expense of the regioselectivity, entry 3.…”

Section: Planar Chiralitymentioning

confidence: 99%

The Development of Enantioselective Rhodium-Catalysed Hydroboration of Olefins

Carroll

O’Sullivan

Guiry

2005

Advanced Synthesis & Catalysis

333

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Rhodium-catalysed enantioselective hydroboration of olefins is a valuable synthetic transformation, typically employing a chiral catalyst and an achiral borane source. The pertinent chemo-, regio-and enantioselectivity issues of this reaction are discussed. However, the main emphasis of this review is on the evolution of catalytic asymmetric hydroboration. This has primarily relied upon the development and application of chiral bidentate P,P and P,N ligands which have exhibited varying degrees of success in this transformation.

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“…[156] These were successfully applied in the rhodium-catalysed hydroboration of styrene with a 92% enantiomeric excess being achieved with 428 although the regioselectivity was poor. Good results were also obtained in the allylic alkylation of 1,3-diphenylallyl where all except 426 gave enantiomeric excesses above 80%.…”

Section: Imidazoline N Donormentioning

confidence: 99%

The Development of Bidentate P,N Ligands for Asymmetric Catalysis

2004

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In this review, an attempt is made to systemise the ro √ le which bidentate phosphinamine (P,N) ligands play in asymmetric catalysis. The ligands will be classified, not by the reaction to which their metal complexes have been applied, but by the nature of their donor atoms. In this manner the development of ligand architectural design can be more easily monitored. The asymmetric transformations to which metal complexes of these ligands have been applied include among others, palladium-catalysed allylic substitutions, copper-catalysed 1,4-additions to enones and rhodiumcatalysed hydroboration of vinylarenes. Excellent enantioselectivities, regioselectivities and reactivities have been achieved in each of these processes.

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New P,N-ferrocenyl ligands for rhodium-catalyzed hydroboration and palladium-catalyzed allylic alkylation

Cited by 50 publications

References 26 publications

Ferrocene-derived P,N ligands: synthesis and application in enantioselective catalysis

Ferrocene-derived P,N ligands: synthesis and application in enantioselective catalysis

The Development of Enantioselective Rhodium-Catalysed Hydroboration of Olefins

The Development of Bidentate P,N Ligands for Asymmetric Catalysis

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