Optically Active Dinuclear Palladium Complexes Containing a Pd−Pd Bond: Preparation and Enantioinduction Ability in Asymmetric Ring-Opening Reactions

Ogura, Tomokazu; Yoshida, Kazuhiro; Yanagisawa, Akira; Imamoto, Tsuneo

doi:10.1021/ol900533h

Cited by 66 publications

(18 citation statements)

References 40 publications

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“…Although the alkylative ARO of oxa/azabicylic alkenes has been demonstrated with hard organometallic reagents,4 the enantioselective alkylative ring opening of oxabicyclo‐[2.2.1]heptanes and azabicyclic alkenes has only been achieved with the use of dimethyl‐ and diethylzinc 2a,b,f. 3c,d In general, the alkylative ARO has been limited in scope due to the instability and lack of accessibility of the organometallic reagents. Consequently, only simple alkyl fragments that lack functional group handles have been reported.…”

Section: Methodsmentioning

confidence: 99%

The Use of Silyl Ketene Acetals and Enol Ethers in the Catalytic Enantioselective Alkylative Ring Opening of Oxa/Aza Bicyclic Alkenes

Zhang

Lautens

2014

Angewandte Chemie

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Silyl ketene acetals and enol ethers are employed as reactive and functional group tolerant nucleophiles in the enantioselective rhodium-catalyzed alkylative ring opening of a diverse class of oxa/azabicyclic alkenes. This method provides access to enantioenriched dihydronaphthalene and cyclohexene scaffolds, which have the potential to be derivatized toward core motifs of naphthoquinone and sesquiterpene natural products. Angewandte Chemie 6061Scheme 4. Azabicyclic alkene scope and derivatization. Absolute stereoconfiguration of 3 q determined by X-ray crystallography. See Supporting Information for details.Scheme 5. Further transformations of ARO products. See Supporting Information for reaction details.

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Section: Methodsmentioning

confidence: 99%

The Use of Silyl Ketene Acetals and Enol Ethers in the Catalytic Enantioselective Alkylative Ring Opening of Oxa/Aza Bicyclic Alkenes

Zhang

Lautens

2014

Angewandte Chemie

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“…Many reports of catalytic processes mediated by dinuclear palladium(I) complexes used as catalyst precursors have been published. Notably, almost all of these studies reported remarkably high efficiencies for the catalytic reactions, which included Suzuki–Miyaura coupling [ 28 ], Sonogashira coupling [ 57 ], Hiyama coupling [ 29 ], Buchwald–Hartwig amination [ 26 ], Kumada–Corriu and Negishi coupling [ 58 ] ( Scheme 1 ), and others [ 59 , 60 , 61 ], suggesting that dinuclear Pd(I) complexes can generate species with unusually high activity as key intermediates. However, in all but a few examples, it was unclear how these reactions proceeded from the dinuclear Pd(I) complexes.…”

Section: Catalytic Applicationsmentioning

confidence: 99%

Dinuclear Nickel(I) and Palladium(I) Complexes for Highly Active Transformations of Organic Compounds

2018

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In typical catalytic organic transformations, transition metals in catalytically active complexes are present in their most stable valence states, such as palladium(0) and (II). However, some dimeric monovalent metal complexes can be stabilized by auxiliary ligands to form diamagnetic compounds with metal–metal bonding interactions. These diamagnetic compounds can act as catalysts while retaining their dimeric forms, split homolytically or heterolytically into monomeric forms, which usually have high activity, or in contrast, become completely deactivated as catalysts. Recently, many studies using group 10 metal complexes containing nickel and palladium have demonstrated that under specific conditions, the active forms of these catalyst precursors are not mononuclear zerovalent complexes, but instead dinuclear monovalent metal complexes. In this mini-review, we have surveyed the preparation, reactivity, and the catalytic processes of dinuclear nickel(I) and palladium(I) complexes, focusing on mechanistic insights into the precatalyst activation systems and the structure and behavior of nickel and palladium intermediates.

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“…Unlike gold, palladium has enjoyed a compelling reputation as a chemically active material. In fact, many palladium compounds including palladium complexes are currently being utilized as catalysts in asymmetric syntheses, [40,41] cross coupling, [42][43][44][45][46] and alkylation reactions. [47,48] Additionally, palladium is known for its uniquely high hydrogen gas absorption capacity, which has been documented to occur even at room temperature and pressure.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Properties of Unsupported Palladium Nanoparticle Surfaces Capped with Small Organic Ligands

Gavia

Shon

2015

ChemCatChem

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This Minireview summarizes a variety of intriguing catalytic studies accomplished by employing unsupported, either solubilized or freely mobilized, and small organic ligand-capped palladium nanoparticles as catalysts. Small organic ligands are gaining more attention as nanoparticle stabilizers and alternates to larger organic supports, such as polymers and dendrimers, owing to their tremendous potential for a well-defined system with spatial control in surrounding environments of reactive surfaces. The nanoparticle catalysts are grouped depending on the type of surface stabilizers with reactive head groups, which include thiolate, phosphine, amine, and alkyl azide. Applications for the reactions such as hydrogenation, alkene isomerization, oxidation, and carbon-carbon cross coupling reactions are extensively discussed. The systems defined as “ligandless” Pd nanoparticle catalysts and solvent (e.g. ionic liquid)-stabilized Pd nanoparticle catalysts are not discussed in this review.

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Optically Active Dinuclear Palladium Complexes Containing a Pd−Pd Bond: Preparation and Enantioinduction Ability in Asymmetric Ring-Opening Reactions

Cited by 66 publications

References 40 publications

The Use of Silyl Ketene Acetals and Enol Ethers in the Catalytic Enantioselective Alkylative Ring Opening of Oxa/Aza Bicyclic Alkenes

The Use of Silyl Ketene Acetals and Enol Ethers in the Catalytic Enantioselective Alkylative Ring Opening of Oxa/Aza Bicyclic Alkenes

Dinuclear Nickel(I) and Palladium(I) Complexes for Highly Active Transformations of Organic Compounds

Catalytic Properties of Unsupported Palladium Nanoparticle Surfaces Capped with Small Organic Ligands

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