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Gold- and Platinum-Catalyzed Reactions of Enynes

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Gold-Catalyzed Cycloisomerization Reactions Through Activation of Alkynes

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Abstract

In this chapter we will introduce the reactivity of enynes toward gold catalysis. As many examples of gold-catalyzed enyne cycloisomerizations have been reported in the literature, we will only focus on examples we found relevant in view of the results that will be presented in the following chapters.

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Notes

  1. 1.

    Seminal report with Co: [8]. With Rh: [9, 10].

  2. 2.

    Seminal report with Ni–Cr: [12]. With Ru: [13].

  3. 3.

    Cyclobutenes could have been isolated in some cases, see: [18, 19].

  4. 4.

    First description of nonclassical cation: [38]. Introduction of the term: [39, 40].

  5. 5.

    This fact was also enforced by some effective skeletal reorganization promoted by either a Lewis or a Brønsted acid.

  6. 6.

    For a review see: [41].

  7. 7.

    For a study on the influence of alkene substituents on the structure of this intermediate see: [61].

  8. 8.

    Selected examples: [78–81].

  9. 9.

    Leading references: [89–100].

  10. 10.

    A similar reactivity with related substrates was observed with W(CO)5(thf), probably through the same type of intermediates: [101, 102].

  11. 11.

    Similar products were obtained with silyl ketene amides and carbamates: [105].

  12. 12.

    Asymmetric versions with Pt: [109–111].

  13. 13.

    Reference [112]. Asymmetric versions: [113, 114].

  14. 14.

    3-hydroxy-1,5-allenynes reacted similarly with Pt: [128].

  15. 15.

    Other ring-enlargement triggered by complexation of gold onto an alkyne: [131–133].

  16. 16.

    Reference [134]. DFT calculations: [135].

  17. 17.

    References [154–156]. See also with Pt: [157].

  18. 18.

    Intramolecular alkoxycyclizations: [157, 158]. Intermolecular alkoxycyclizations: [159].

  19. 19.

    With Ru: [183–186]. This study shows that the use of enantioenriched propargyglic acetates results in racemic cyclopropane, but good ees were obtained using chiral gold catalysts. See also: [187].

  20. 20.

    References [193–195]. See also: [196–198].

  21. 21.

    Selected examples with Pt: Ref. [168] and also [206, 207]. With Au: [208–211].

  22. 22.

    Reference [212]. For a theoretical study see: [213].

  23. 23.

    Some examples are described in the following review: [219].

  24. 24.

    Comparable products were also obtained from the cyclization of 1,6-enynes with stoiechiometric amounts of TiCl4: [220].

  25. 25.

    Ligand effects in gold catalysis have been recently reviewed, see: [225].

  26. 26.

    Gold’s “alkynophilicity” results in a preferred reaction of activated alkynes rather than activated allenes. However, some reports dealing with allenynes are consistent with initial activation of the allene, see: [226–228]. See also ref. [128].

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    Antoine Simonneau

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Simonneau, A. (2014). Gold- and Platinum-Catalyzed Reactions of Enynes. In: Gold-Catalyzed Cycloisomerization Reactions Through Activation of Alkynes. Springer Theses. Springer, Cham. https://doi.org/10.1007/978-3-319-06707-0_1

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