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Harnessing Reversible Oxidative Addition: Application of Diiodinated Aromatic Compounds in Aryliodination

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Book cover Stereoselective Heterocycle Synthesis via Alkene Difunctionalization

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Abstract

The previous chapters have highlighted the positive impact that Pd-catalyzed cross-coupling reactions have had on the chemical sciences. The use of substrates that are pre-functionalized with a carbon–halogen bond allows for a high degree of regiocontrol since the Pd(0) catalyst has a high propensity to undergo oxidative addition at this site. However, these reactions become less predictable once more than one carbon–halogen bond is present in the substrate.

Portions of this chapter have appeared in print. See: Refs. [1, 2].

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Notes

  1. 1.

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  2. 2.

    The use of pseudohalides (i.e. OTf or OTs) can also be used to impart selectivity.

  3. 3.

    Reference [6].

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  6. 6.

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  12. 12.

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  14. 14.

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  15. 15.

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  18. 18.

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  19. 19.

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  20. 20.

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  21. 21.

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  22. 22.

    Complex 4.68 could also be generated in 85% by treatment of 4.65 with BzCl in pentane at RT for 1 h.

  23. 23.

    Reference [29].

  24. 24.

    Reference [32].

  25. 25.

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  27. 27.

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  28. 28.

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  29. 29.

    Reference [39].

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Author notes

  1. David A. Petrone

    Present address: Laboratory for Organic Chemistry, ETH Zürich, Zürich, Switzerland

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    Petrone, D.A. (2018). Harnessing Reversible Oxidative Addition: Application of Diiodinated Aromatic Compounds in Aryliodination. In: Stereoselective Heterocycle Synthesis via Alkene Difunctionalization. Springer Theses. Springer, Cham. https://doi.org/10.1007/978-3-319-77507-4_4

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