Concepedia

Efficient Cross-Coupling Reactions of Aryl Chlorides and Bromides with Phenyl- or Vinyltrimethoxysilane Mediated by a Palladium/Imidazolium Chloride System

Hon Man Lee, Steven P. Nolan

Organic Letters · 2000 · 191 citations · 30 references

DOI

Concepts

Abstract

A combination of palladium acetate and the imidazolium salt IPr.HCl (1, IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) has proven to be highly efficient in the cross coupling reactions of aryl bromides and electron-deficient aryl chlorides with phenyltrimethoxysilane or vinyltrimethoxysilane. The catalytic performance of this system was found to be comparable to that of systems using PCy(3) and P(o-tol)(3).

References

30

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Dietmar Seyferth · Organometallics · 1984 · 4.8K citations

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The Palladium‐Catalyzed Cross‐Coupling Reactions of Organotin Reagents with Organic Electrophiles [New Synthetic Methods (58)]

J. K. Stille · Angewandte Chemie International Edition in English · 1986 · 3.4K citations

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Dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium(II): an effective catalyst for cross-coupling of secondary and primary alkyl Grignard and alkylzinc reagents with organic halides

Tamio Hayashi, Mitsuo Konishi, Yuji Kobori et al. · Journal of the American Chemical Society · 1984 · 747 citations

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Nickel-Phosphine Complex-Catalyzed Grignard Coupling. I. Cross-Coupling of Alkyl, Aryl, and Alkenyl Grignard Reagents with Aryl and Alkenyl Halides: General Scope and Limitations

Kohei Tamao, Koji Sumitani, Yoshihisa Kiso et al. · Bulletin of the Chemical Society of Japan · 1976 · 589 citations · Full text

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Palladium−Imidazol-2-ylidene Complexes as Catalysts for Facile and Efficient Suzuki Cross-Coupling Reactions of Aryl Chlorides with Arylboronic Acids

Chunming Zhang, Jinkun Huang, Mark L. Trudell et al. · The Journal of Organic Chemistry · 1999 · 447 citations

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