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Related Experiment Videos

New Efficient Nickel-Catalyzed Cross-Coupling Reaction between Two Csp(3) Centers.

Riccardo Giovannini1, Thomas Stüdemann, Arokiasamy Devasagayaraj

  • 1Fachbereich Chemie der Philipps-Universität Marburg, Hans-Meerwein-Strasse, D-35043 Marburg, Germany, and Institut für Organische Chemie der Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13, D-81377 München, Germany.

The Journal of Organic Chemistry
|October 25, 2001
PubMed
Summary

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Remote unsaturation in alkyl halides enables cross-coupling with diorganozincs using Ni(acac)(2) catalyst. This facilitated a new reaction for polyfunctional products, using trifluoromethylstyrene as a promoter.

Area of Science:

  • Organic Chemistry
  • Organometallic Chemistry

Background:

  • Remote unsaturation in alkyl halides can influence reactivity.
  • Nickel-catalyzed cross-coupling reactions are vital in organic synthesis.

Purpose of the Study:

  • To investigate the effect of remote unsaturation on alkyl halide cross-coupling.
  • To develop a novel cross-coupling method for polyfunctional products.

Main Methods:

  • Cross-coupling reactions using alkyl halides with remote unsaturation and diorganozincs.
  • Utilizing Ni(acac)(2) as a catalyst in THF/NMP mixtures.
  • Developing a new reaction employing m- or p-trifluoromethylstyrene as a promoter.

Main Results:

  • Remote unsaturation significantly facilitates cross-coupling reactions.

Related Experiment Videos

  • A new general cross-coupling reaction was established for functionalized diorganozincs and alkyl iodides.
  • The reaction produced a broad range of polyfunctional cross-coupling products.

    • Conclusions:

    • Remote unsaturation is a key factor in facilitating nickel-catalyzed cross-coupling of alkyl halides.
    • The developed method offers a versatile route to complex polyfunctional molecules.
    • Trifluoromethylstyrene acts as an effective reaction promoter in this system.