Nickel-Catalyzed Asymmetric Synthesis of P-Stereogenic Vinyl Phosphines

Liu, Xu-Teng; Wu, Yue; Zhang, Qing‐Wei

doi:10.1055/a-1695-4979

Cited by 4 publications

(1 citation statement)

References 47 publications

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“…In 2021, Liu and Lu reported the formation of benzimidazole atropisomers using intramolecular cyclization chemistry involving amidines (Scheme 19). [69,70] Amidines 59 derived from commercially available anilines were treated with palladium and the chiral (S)-BINAP ligand to afford annulation products 60 or 61 bearing one or two chiral axes. The protocol exhibited broad substrate scope and included a diverse set of substituents at various positions of the benzimidazole and aryl ring.…”

Section: Cà N Atropisomer Synthesismentioning

confidence: 99%

The Asymmetric Buchwald–Hartwig Amination Reaction

Feng

et al. 2023

Angewandte Chemie

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Over the past few decades, the Buchwald-Hartwig reaction has emerged as a powerful tool for forging CÀ N bonds, and has been vital to the pharmaceuticals, materials, and catalysis fields. However, asymmetric Buchwald-Hartwig amination reactions for constructing centered chirality, planar chirality, and axial chirality remain in their infancy owing to limited substrate scope and laggard ligand design. The recent surge in interest in the synthesis of CÀ N/ NÀ N atropisomers, has witnessed a renaissance in asymmetric Buchwald-Hartwig amination chemistry as the first practical protocol for the preparation of CÀ N atropisomers. This review highlights reported asymmetric Buchwald-Hartwig amination protocols and provides a brief overview of their chemical practicality.

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Section: Cà N Atropisomer Synthesismentioning

confidence: 99%

The Asymmetric Buchwald–Hartwig Amination Reaction

Feng

et al. 2023

Angewandte Chemie

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The Asymmetric Buchwald–Hartwig Amination Reaction

Feng

et al. 2023

Angew Chem Int Ed

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Over the past few decades, the Buchwald–Hartwig reaction has emerged as a powerful tool for forging C−N bonds, and has been vital to the pharmaceuticals, materials, and catalysis fields. However, asymmetric Buchwald–Hartwig amination reactions for constructing centered chirality, planar chirality, and axial chirality remain in their infancy owing to limited substrate scope and laggard ligand design. The recent surge in interest in the synthesis of C−N/N−N atropisomers, has witnessed a renaissance in asymmetric Buchwald–Hartwig amination chemistry as the first practical protocol for the preparation of C−N atropisomers. This review highlights reported asymmetric Buchwald–Hartwig amination protocols and provides a brief overview of their chemical practicality.

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Exploring Electrophilic Hydrophosphination via Metal Phosphenium Intermediates

Belli,

Muir,

Dyck

et al. 2024

Chemistry A European J

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Two Mo(0) phosphenium complexes containing ancillary secondary phosphine ligands have been investigated with respect to their ability to participate in electrophilic addition at unsaturated substrates and subsequent P‐H hydride transfer to “quench” the resulting carbocations. These studies provide stoichiometric “proof of concept” for a proposed new metal‐catalyzed electrophilic hydrophosphination mechanism. The more strongly Lewis acidic phosphenium complex, [Mo(CO)4(PR2H)(PR2)]+ (R = Ph, Tolp), cleanly hydrophosphinates 1,1‐diphenylethylene, benzophenone, and ethylene, while other substrates react rapidly to give products resulting from competing electrophilic processes. A less Lewis acidic complex, [Mo(CO)3(PR2H)2(PR2)]+, generally reacts more slowly but participates in clean hydrophosphination of a wider range of unsaturated substrates, including styrene, indene, 1‐hexene, and cyclohexanone, in addition to 1,1‐diphenylethylene, benzophenone, and ethylene. Mechanistic studies are described, including stoichiometric control reactions and computational and kinetic analyses, which probe whether the observed P‐H addition actually does occur by the proposed electrophilic mechanism, and whether hydridic P‐H transfer in this system is intra‐ or intermolecular. Preliminary reactivity studies indicate challenges that must be addressed to exploit these promising results in catalysis.

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Nickel-Catalyzed Asymmetric Synthesis of P-Stereogenic Vinyl Phosphines

Cited by 4 publications

References 47 publications

The Asymmetric Buchwald–Hartwig Amination Reaction

The Asymmetric Buchwald–Hartwig Amination Reaction

The Asymmetric Buchwald–Hartwig Amination Reaction

Exploring Electrophilic Hydrophosphination via Metal Phosphenium Intermediates

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